Bibliographies thématiques / Synthesis of thioamide

Littérature scientifique sur le sujet « Synthesis of thioamide »

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Publié le 18 mai 2024

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Articles de revues sur le sujet "Synthesis of thioamide"

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Dong, Zhi-Bing, Meng-Tian Zeng, Min Wang, Han-Ying Peng et Yu Cheng. « Copper-Catalyzed Synthesis of Aryl Thioamides from Aryl Aldehydes and Tetramethylthiuram Disulfide ». Synthesis 50, no 03 (12 octobre 2017) : 644–50. http://dx.doi.org/10.1055/s-0036-1590936.

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A novel and convenient method for the synthesis of aryl thioamides from aryl aldehydes and tetramethylthiuram disulfide (TMTD) without the use of sulfurating reagent was explored. In the presence of CuI and di-tert-butyl peroxide (DTBP), various aryl thioamides were prepared with good to excellent yields, tetramethylthiuram disulfide as thioamide source is essential for this transformation. The protocol features broad substrate scope, nice yields, operability and commercially available and inexpensive raw materials, showing its practical synthetic value in organic synthesis.
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Sauvé, Gilles, Vanga S. Rao, Gilles Lajoie et Bernard Belleau. « Backbone-modified oligopeptidic bioregulators. The synthesis and configuration of thioamide, amidoxime, cyanoamidine, and amidrazone analogs of the chemotactic peptide N-formyl-methionyl-leucyl-phenylalanine (f-Met-Leu-Phe-OR) ». Canadian Journal of Chemistry 63, no 11 (1 novembre 1985) : 3089–101. http://dx.doi.org/10.1139/v85-511.

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Reaction conditions for the synthesis of thioamide, amidoxime, and N-substituted amidine analogs of the peptide bond are described. Several new amidine analogs of the chemotactic peptide f-Met-Leu-Phe-OR were synthesized using the thioamides as precursors. The assignment of the E/Z configuration was accomplished by nuclear magnetic resonance. The biological activity of these analogs is briefly described.
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Fong, Mei, Wit K. Janowski, Rolf H. Prager et Max R. Taylor. « A Convenient Synthesis of 2-Substituted Thiazole-5-carboxylates ». Australian Journal of Chemistry 57, no 6 (2004) : 599. http://dx.doi.org/10.1071/ch03252.

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The photolysis of ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxylate in acetonitrile containing 0.5% tri- fluoroacetic acid in the presence of thioamides gives moderate (40–60%) yields of thiazole-5-carboxylate esters. In the absence of trifluoroacetic acid, the intermediate vinyl thioesters can be isolated. That addition of the thioamide to the first formed carbene was, through sulfur, confirmed by X-ray crystal structures of 2-methylthiazole-5-carboxylic acid and a byproduct.
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Szantai-Kis, D., Christopher Walters, Taylor Barrett, Eileen Hoang et E. Petersson. « Thieme Chemistry Journals Awardees – Where Are They Now ? Improved Fmoc Deprotection Methods for the Synthesis of Thioamide-Containing Peptides and Proteins ». Synlett 28, no 14 (19 mai 2017) : 1789–94. http://dx.doi.org/10.1055/s-0036-1589027.

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Site-selective incorporation of thioamides into peptides and proteins provides a useful tool for a wide range of applications. Current incorporation methods suffer from low yields as well as epimerization. Here, we describe how the use of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) rather than piperidine in fluorenylmethyloxycarbonyl (Fmoc) deprotection reduces epimerization and increases yields of thioamide-containing peptides. Furthermore, we demonstrate that the use of DBU avoids byproduct formation when synthesizing peptides containing side-chain thioamides.
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Zhang, Qiang, Laurent Soulère et Yves Queneau. « Towards More Practical Methods for the Chemical Synthesis of Thioamides Using Sulfuration Agents : A Decade Update ». Molecules 28, no 8 (17 avril 2023) : 3527. http://dx.doi.org/10.3390/molecules28083527.

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Compounds possessing a thioamide function play a crucial role in organic synthesis, serving as key building blocks. They are also important in the pharmaceutical chemistry and drug design, owing to their ability to mimic the amide function in biomolecules while retaining or developing biological activity. From the synthetic viewpoint, several methods have been developed for preparing thioamides using sulfuration agents. The purpose of this review is to give an update of the last decade of contributions focusing on the formation of thioamides employing different sulfur sources. When appropriate, the cleanness and practicality of the new methods are highlighted.
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Pham Xuan Thao. « Study on the synthesis of thioamides from aldehyde N-tert-butylsulfinyl amide and sulfur in aqueous media ». Journal of Military Science and Technology, no 76 (12 décembre 2021) : 54–60. http://dx.doi.org/10.54939/1859-1043.j.mst.76.2021.54-60.

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Thioamides have been widely used in the fields of medicine and organic chemistry, some of which are essential bioactive compounds, plant protection agents, and drugs. It could also be used as a vulcanizing agent, an additive to lubricants and greases, and a ligand in organic synthesis. Usually, thioamide is synthesized at high temperatures or in the microwave using an expensive noble metal complex as catalysts. This paper presented a straightforward method for synthesizing thioamides by using N-tert-butylsulfinyl amide, aldehyde, and sulfur. The reaction was carried out in water, which is an environmentally friendly solvent. The reaction selectivity and yield were up to 89%.
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Hammam, A. S., et B. E. Bayoumy. « Reaction of thioamides with 2,3-dichloro-1,4-naphthoquinone. A novel synthesis of naphtho[2,3-d]thiazole-4,9-diones ». Collection of Czechoslovak Chemical Communications 50, no 1 (1985) : 71–79. http://dx.doi.org/10.1135/cccc19850071.

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The reaction of thioamide II with 2,3-dichloro-1,4-naphthoquinone (I) in ethanol gave naptho[2,3-d]thiazole-4,9-diones (IV). The intermediates, 2-thioamido-3-chloro-1,4-naphthoquinones III were also isolated from the reaction medium and could be separately transformed to IV by further boiling in aqueous ethanol containing bicarbonate. The reaction of thiosemicarbazide with I under similar conditions gave naphtho[2,3-e]-2-amino-4H-1,3,4-thiadiazine-5,10-dione (VII).
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Sharma, Shubham, Dharmender Singh, Sunit Kumar, Vaishali, Rahul Jamra, Naveen Banyal, Deepika, Chandi C. Malakar et Virender Singh. « An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy : synthesis of pyrazole-conjugated thioamides and amides ». Beilstein Journal of Organic Chemistry 19 (2 mars 2023) : 231–44. http://dx.doi.org/10.3762/bjoc.19.22.

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An operationally simple and metal-free approach is described for the synthesis of pyrazole-tethered thioamide and amide conjugates. The thioamides were generated by employing a three-component reaction of diverse pyrazole C-3/4/5 carbaldehydes, secondary amines, and elemental sulfur in a single synthetic operation. The advantages of this developed protocol refer to the broad substrate scope, metal-free and easy to perform reaction conditions. Moreover, the pyrazole C-3/5-linked amide conjugates were also synthesized via an oxidative amination of pyrazole carbaldehydes and 2-aminopyridines using hydrogen peroxide as an oxidant.
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Yeo, Chien, et Edward Tiekink. « O-Methyl m-Tolylcarbamothioate ». Molbank 2018, no 3 (15 septembre 2018) : M1020. http://dx.doi.org/10.3390/m1020.

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The synthesis, spectroscopic, and crystallographic characterisation of the title compound, O-methyl m-tolylcarbamothioate, MeOC(=S)N(H)(m-tolyl) (1), are described. The crystallographic study confirms the structure determined by spectroscopy and shows the presence of the thioamide tautomer, a syn-disposition of the thione-S and thioamide-N-H atoms and, in the crystal, thioamide-N-H…S(thione) hydrogen bonding leading to an eight-membered {…HNCS}2 synthon.
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Cakmak, M., I. I. Ozturk, C. N. Banti, M. Manoli, E. Moushi, A. J. Tasiopoulos, A. M. Grześkiewicz, M. Kubicki et S. K. Hadjikakou. « Bismuth(III) bromide-thioamide complexes : synthesis, characterization and cytotoxic properties ». Main Group Metal Chemistry 41, no 5-6 (27 novembre 2018) : 143–54. http://dx.doi.org/10.1515/mgmc-2018-0035.

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Abstract New bismuth(III) bromine compounds of the heterocyclic thioamides were prepared and structurally characterized. The reaction of heterocyclic thioamides with bismuth(III) bromide resulted in the formation of the {[BiBr2(μ2-Br)(MMI)2]2·CH3COCH3·H2O} (1), {[BiBr2(MBZIM)4]·Br·2H2O} (2), {[BiBr2(μ2-Br)(tHPMT)2]2·CH3CN} (3), {[BiBr2(μ2-Br)(PYT)2]2·CH3CN} (4) and {[BiBr2(μ2-Br)(MBZT)2]2 2CH3OH} (5) complexes (MMI: 2-mercapto-1-methylimidazole, MBZIM: 2-mercaptobenzimidazole, tHPMT: 2-mercapto-3,4,5,6-tetrahydro-pyrimidine, PYT: 2-mercaptopyridine and MBZT: 2-mercaptobenzothiazole). The complexes 1–5 were characterized by melting point (m.p.), elemental analysis (e.a.), molar conductivity, Fourier-transform infrared (FT-IR), Fourier-transform Raman (FT-Raman), nuclear magnetic resonance (1H and 13CNMR) spectroscopy, UV-Vis spectroscopy and thermogravimetric-differential thermal analysis (TG-DTA). The molecular structures of 1–5 were determined by single-crystal X-ray diffraction. Complex 2 is a first ionic monomuclear octahedral bismuth(III) bromide, while the complexes 1, 3–5 are the first examples of dinuclear bismuth(III) bromide derivatives. Complexes 1–5 were evaluated in terms of their in vitro cytotoxic activity against human adenocarcinoma breast (MCF-7) and cervix (HeLa) cells. The toxicity on normal human fetal lung fibroblast cells (MRC-5) was also evaluated. Moreover, the complexes 1–5 and free heterocyclic thioamide ligands were studied upon the catalytic peroxidation of the linoleic acid by the enzyme lipoxygenase (LOX).
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Thèses sur le sujet "Synthesis of thioamide"

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Brandes, Dee Anne. « The synthesis and reactivity of alpha,beta-unsaturated thioamide, thioester, and thione iron tricarbonyl complexes ». Thesis, University of Ottawa (Canada), 1990. http://hdl.handle.net/10393/6008.

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$\alpha,\beta$-Unsaturated thioamide, thioester and thione iron tricarbonyl complexes 1-13 were prepared from the free ligands and iron pentacarbonyl using photolysis or diiron nonacarbonyl using thermolysis. X-ray crystal structures were obtained for the free ligand 2$\sp\prime,$ (PhCH=C(Ph)C(S)NEt$\sb2$), and for complexes 1 and 2, $\rm\lbrack \overline{\overline{Fe(PhCH}{=}CHC(S})NEt\sb2)$(CO)$\sb3\rbrack$ and $\rm\lbrack \overline{\overline{Fe(PhCH}{=}C(Ph)C(S})NEt\sb2)$(CO)$\sb3\rbrack$ respectively. Thioamide and thioester iron tricarbonyl complexes gave triphenylphosphine substituted complexes 17-19 resulting from loss of a carbon monoxide ligand by photolysis or thermolysis. It was not possible to substitute more than one triphenylphosphine into the complexes. Thioamide and thioester ligands could be removed from the iron tricarbonyl fragment using ceric ammonium nitrate, hydrogen peroxide, m-chloroperbenzoic acid, or thermolysis. The best results were obtained with ceric ammonium nitrate, which minimized conversion of the C=S functional group to C=O. Thioester complex 10, $\rm\lbrack \overline{\overline{Fe(PhCH}{=}CHC(S})OEt)(CO)\sb3\rbrack,$ reacted with hydrogen peroxide or m-chloroperbenzoic acid to give the sulphine complex 20, $\rm\lbrack \overline{\overline{Fe(PhCH}{=}CHC(S}{=}O)OEt)(CO)\sb3\rbrack.$ Nucleophiles reacted with thioamide and thioester iron tricarbonyl complexes at room temperature affording 1,4-Michael addition products free of metal coordination. At $-$78$\sp\circ$C, nucleophiles reacted with thioamide iron tricarbonyl complexes forming 4-oxo-thioamide non-metal coordinated products. An electrophile reacted with thioester tricarbonyl complex 10 to give an S-alkylated cationic complex 21, $\rm\lbrack\lbrack\overline{\overline{Fe(PhCH}{=}CHC(S} {\sp+}$-Me)OEt)(CO)$\sb3 \rm\rbrack \lbrack BF\sb4\sp-\rbrack\rbrack.$ Alkynes added to the metal-coordinated olefin of $\alpha,\beta$-unsaturated thioamide iron tricarbonyl complexes 1, 4, $\rm\lbrack\overline{\overline{Fe(MeCH}{=}CHC(S})NEt\sb2)$(CO)$\sb3\rbrack,$ and 7, $\rm\lbrack\overline{\overline{Fe(MeCH}{=}CHC(S})N(Ph)$(Me))(CO)$\sb3\rbrack,$ generating complexes 22-26 possessing a cyclopentenone ligand. An X-ray crystal structure was obtained for complex 22. Silicon alkoxides were used as a source of alkoxide to prepare carboxylic esters in good yields from benzylic bromides and carbon monoxide catalyzed by a rhodium (I) complex under mild conditions.
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Mukherjee, Suvodip. « Methodological approach on carbon-hetero bond formation reaction ». Thesis, University of North Bengal, 2022. http://ir.nbu.ac.in/handle/123456789/4792.

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Kienz, Torben [Verfasser]. « Exploration of N-ferrocenyl substituted thioamides : synthesis, properties and reactivity / Torben Kienz ». Mainz : Universitätsbibliothek Mainz, 2016. http://d-nb.info/1120619912/34.

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Ellwood, A. R. « A synthetic approach to the sarain core and development of new thioamide-based methodologies ». Thesis, University College London (University of London), 2011. http://discovery.ucl.ac.uk/1332893/.

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Sarain A is a marine alkaloid that was isolated from the Mediterranean sponge Reniera sarai; the alkaloid possesses antibacterial, insecticidal and antitumour properties. As a result of the intriguing structure of this alkaloid, it has quickly become a popular target for organic chemists. Arguably the most challenging part of its synthesis is the tricyclic core, which is surrounded by two macrocyclic rings. This thesis describes two separate approaches towards the core, both utilising a thia-Claisen rearrangement as a key step. The first approach involved the ring expansion of a 5,5-bicyclic aminal to form an iminium ion intermediate which could be transformed into the core. However, the inherent lack of nucleophilicity of an N-tosyl sulfonamide nitrogen atom in the bicyclic aminal made it difficult to perform the ring expansion. The second method involved a modification of an acid catalysed rearrangement previously attempted within the Porter group; in the previous approach, a differentially protected bicyclic aminal opened with cleavage of a C-NTs rather than a C-NBn bond, leading to an undesired tricyclic product. In the newly devised route, the protecting groups on the two nitrogen atoms of the bicycle were reversed in order to encourage ring opening in the desired fashion; however, the only attempt at this step did not result in the formation of the sarain core. In a different project that is related to the aforementioned research, a diastereoselective thia-Claisen rearrangement was developed which allows the formation of a key intermediate en route to the sarain core, in enantiomerically pure form. To achieve this, thia-Claisen rearrangements were carried out on several S-allyl N,S-ketene acetals bearing a stereogenic centre on the allyl portion of the molecule to give diastereomeric ratios of 2:1 to 30:1. Interestingly, introduction of a bromine atom onto the double bond of the allylic portion of the precursor increased and reversed the diastereoselectivity. Finally, following a discovery that was made whilst working towards the sarain core, a novel reaction for the high-yielding conversion of a wide range of alcohols into iodides using a thioiminium salt has been investigated and optimised. The reaction conditions are essentially neutral, no aqueous workup is required, many functional groups can be tolerated and reaction times are generally short. Furthermore, the thioiminium salt can be stored for long periods without degradation. This type of chemistry has since been further examined, and it can now be used to allow the conversion of alcohols directly into sulfide products that are precursors in Julia-Kocienski reactions.
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LELONG, BRUNO. « Synthese diastereoselective de thioamides ' et -dihydroxyles : une voie d'acces aux valerolactones ». Caen, 1997. http://www.theses.fr/1997CAEN2059.

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L'objectif de ce travail est l'hydroboration chimio- et diastereoselective de composes thiocarbonyles -insatures. Ces molecules sont en effet de bons precurseurs pour synthetiser des valerolactones de facon assez simple. Apres avoir montre que la reaction d'hydroboration n'est pas chimioselective vis a vis des dithioesters, et constate que la reaction d'hydroboration sur les dithiocetals -ethyleniques n'est pas diastereoselective, nous nous sommes tournes vers la fonction thioamide pour acceder aux lactones. Les -hydroxythioamides -ethyleniques requis sont synthetises par thiorearrangement de claisen des -hydroxyaminothiocetals de cetene de s-allyle correspondants. Le diastereoisomere syn est obtenu de facon majoritaire (ed 70%). Un modele pseudocyclique chaise explique cette configuration majoritaire. L'hydroboration des -hydroxythioamides -ethyleniques syn est chimioselective et conduit aux thioamides dihydroxyles syn-anti majoritairement. Ces dihydroxythioamides syn-anti sont cyclises en valerolactones de configuration trans. Cette configuration a ete etablie par rmn #1#3c et par effet noe et elle permet d'attribuer une configuration anti au produit obtenu lors de l'hydroboration. Nous proposons un modele sans chelation bore-soufre afin d'expliquer cette selectivite anti. Nous avons enfin ouvert une nouvelle voie de synthese des trans -lactones a partir des -hydroxythioamides -ethyleniques anti.
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ABOUSAID, LEKBIR. « Etude cinetique de la thioamidation en serie aromatique. Synthese et caracterisation des (co)polyamide-thioamides ». Caen, 1996. http://www.theses.fr/1996CAEN2031.

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Les bis(dithioester)s iso et terephtaliques ont ete synthetises a partir de bis(chloromethyl)benzene ou des diacides phtaliques. La reaction d'un exces de diamines sur ces composes conduit a la formation de nombreux bis(thioamide-amine)s et bis(thioamide)s derives avec de bons rendements. Associes au chlorure de phtaloyle, les bis(thioamide-amine)s ont donne des (co)polyamide-thioamides amorphes contenant de nombreuses structures cycliques. Ces nouveaux copolymeres ont ete caracterises par spectroscopie #1h, #1#3c rmn, ir, uv-vsible, mesure de viscosite et analyse enthalpique differentielle (dsc). Les temperatures de transition vitreuses (tg) de ces copolymeres sont elevees. La rigidite moleculaire de ces nouveaux copolymeres peut devenir tres elevee si on tient compte de l'absence de rotation libre dans les groupes amides et thioamides, leur solubilite est donc tres limitee ce qui est une gene pour leur caracterisation. La cinetique de thioacylation des amines aliphatiques par les bis(dithioester)s iso et terephtalique realisee en solution a temperature ambiante a mis en evidence un ordre trois quelles que soient les conditions employees. Les valeurs observees pour la constante de vitesse d'ordre trois sont en accord avec les reactions legerement plus lentes des dithioesters conjugues benzeniques, de plus les constantes de vitesse k#i#i#i varient en fonction de la nature des reactifs et de la polarite des solvants. L'energie d'activation de l'ordre de 30 kj mol#-#1 reste moderee mais plus elevee qu'en serie aliphatique, ce qui s'explique par l'influence de la conjugaison
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Rodriguez-Garcia, Valerie. « Efficient methodology for the synthesis of 2,4-benzodiazepin-1-ones, sulfonylbenzotriazoles, sulfonamides, ethylene sulfonamides, thiocarbamates, dithiocarbamates and thioamides ». [Gainesville, Fla.] : University of Florida, 2004. http://purl.fcla.edu/fcla/etd/UFE0006303.

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Kulesza, Joanna. « Synthesis and studies of binding properties of calix[4]arenes functionalised with amide and hydroxamate moities and their thiocarbonyl analogues ». Strasbourg, 2011. http://www.theses.fr/2011STRA6093.

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Afin de pouvoir suivre les teneurs en cations de métaux lourds toxiques pour les organismes vivants tels que Pb2+ ou Cd2+, il est nécessaire de concevoir des composés hautement sélectifs. Ce travail porte sur la synthèse et l’étude de dérivés amides et hydroxyamides de calix[4]arènes et de leurs analogues thiocarbonylés. Vingt sept dérivés (thioamides, amides, hydroxamates et acides hydroxamiques) ont été obtenus. Différentes techniques ont permis l’étude des interactions entre ces ligands et des cations métalliques: spectroscopie RMN du 1H, diffraction des rayons X, extraction liquid-liquid, spectrophotométrie d’absorption dans l’UV, potentiométrie et microcalorimétrie. Le remplacement des atomes d’oxygène des amides tertiaires par des atomes de soufre conduit à des composés très sélectifs pour Ag+ et Pb2+ par rapport aux cations des groupes I et II. Les dérivés acides hydroxamiques extraient très efficacement Fe3+ et Cu2+. Des résultats intéressants ont été obtenus avec ces composés permettant d’envisager l'élimination et la séparation de Pb2+ d'autres métaux toxiques comme Cd2+. De plus, l’utilisation de ces ligands pourrait permettre de séparer Cu2+ de Zn2+ et Ni2+ qui sont souvent présents simultanément. Les dérivés thioamides et hydroxamates ont été utilisés comme éléments sensibles dans la membrane d’électrodes sélectives (ISEs). Les électrodes basées sur des dérivés thioamides, en particulier sur les composés porteurs de fonctions piperidinyles et morpholinyles devraient permettre le développement d’outils analytiques prometteurs pour le contrôle des niveaux de pollution en Pb2+ dans les eaux naturelles et les eaux potables
The need of monitoring and controlling the concentration of heavy metal ions such as Pb2+ or Cd2+, which have toxic effects on all living organisms inspires chemists to synthesise more and more selective compounds. The aim of this work was the synthesis of amide and hydroxyamide derivatives of calix[4]arenes and their thiocarbonyl analogues. Nine thioamide derivatives as well as their respective amide derivatives, five hydroxamate derivatives and four calix[4]arene-hydroxamic acids were obtained. Studies of ligands interaction with metal cations were investigated using different techniques: 1H NMR spectroscopy, X-ray diffraction, liquid-liquid extraction, UV absorption spectrophotometry, potentiometry and microcalorimetry. The replacement of the oxygen atoms by sulphur atoms in the tertiary amide structures led to compounds highly selective for Ag+ and Pb2+ over I and II group of cations. Hydroxamic acids of calix[4]arene occurred to be efficient extractants for Fe3+ and Cu2+. Moreover, very important results obtained with these compounds could find an application in the context of the removal and separation of Pb2+ from other toxic metals such as Cd2+. In addition, these ligands could be used to separate Cu2+ from Ni2+ and Zn2+, which are often found together. Selectivity of thioamide and hydroxamate derivatives was assessed using these ligands as sensor materials in ion-selective membrane electrodes. Electrodes based on calix[4]arene-thioamides, particularly on compounds bearing piperidinyl and morpholinyl substituents are promising analytical tools for monitoring Pb2+ concentration in natural and drinking waters
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Mykhaylychenko, Sergiy. « Study of perfluoroketene dithioacetals and N,S-acetals for the synthesis of fluorinated acyclic and heterocyclic compounds ». Rouen, 2008. http://www.theses.fr/2008ROUES066.

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Les dithioacétals de perfluorocétènes sont des « synthons » simples et polyvalents pour la synthèse d'une large variété de composés fluorés acycliques et cycliques. Des transformations efficaces et directes des g-lactones a,b-insaturées en g-lactames et en pyridazin-3-ones substitués par un groupement 2,2,2-trifluoroéthyle ont été effectuées, à partir d'amines primaires et d'hydrazines variées et des dithioacétals de perfluorocétènes. La structure de tous les nouveaux composés a été assignée en utilisant les données de RMN (19F, 1H, 13C), d'IR et de MS et par diffraction des rayons X. Les réactions des polyfluorothioamides N-monosubstitués avec des réactifs organolithiums ont été étudiées. Dans le cas des polyfluorothioamides N,N-disubstitués, les N,S-acétals ont été obtenus. Les propriétés chimiques des N,S-acétals de perfluorocétènes, incluant les réactions d'oxydation et de chloration, ont été étudiées. La réaction d'oxydation des N,S-acétals de perfluorocétènes avec l'hydroperoxyde de tertbutyle a conduit à la formation d'un a-hydroperfluoroamide. La chloration des N,S-acétals de perfluorocétènes avec le chlorure de sulfuryle a donné des a-chloroperfluoroamides ; cette méthode s'est avérée une nouvelle approche pour la synthèse des composés polyfluorés a-chlorés optiquement actifs. Les mécanismes possibles pour ces transformations ont été discutés
Perfluoroketene dithioacetals are simple and highly versatile building-blocks for the synthesis of various fluorinated acyclic and heterocyclic compounds. Efficient and straightforward transformation of a,b-unsaturated g-lactones into 2,2,2-trifluoroethyl substituted γ-lactams and pyridazin-3-ones was performed, starting from a variety of primary amines or hydrazines and perfluoroketene dithioacetatals. The structures of all new compounds were ascribed using NMR (19F, 1H, 13C), IR, MS data and X-ray diffraction analysis. The possible mechanisms for the formation of γ-lactams and pyridazin-3-ones are also presented. The reactions of N-monosubstituted polyfluorothioamides with alkyllithium reagents were studied. In the case of N,N-disubstituted perfluorothioamides N,S-acetals were obtained. Some chemical properties of perfluoroketene-N,S-acetals, including oxidation and chlorination reactions, were investigated. Oxidation reaction of perfluoroketene-N,S-acetals with t-butylhydroperoxide led to a formation of a-hydroperfluoroamides. Chlorination of perfluoroketene-N,S-acetals with sulfuryl chloride gave a-chloroperfluoroamides; this method proved to be a new approach in the synthesis of polyfluorinated a-chloro optically active compounds. The possible mechanisms for these transformations are discussed
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Khatri, Bhavesh. « Exploring Nature's Inventory : Investigating the Role of Amide to Thioamide Substitution on Protein Stability ». Thesis, 2020. https://etd.iisc.ac.in/handle/2005/5635.

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The peptide backbone holds a protein together and plays a crucial role in guiding its three-dimentional structure. The tertiary structure of proteins regulates several biological processes. Therefore, peptide bond modification has gained significant attention to influence protein folding, stability, and functions. However, it is a challenging task to mimic the peptide (amide) bond due to its unique properties, such as planar structure, hydrogen bond donor, and acceptor properties. Thioamide, a single O to S substitution in an amide bond, is the closest isostere and has shown promising results on small peptides. The recent discovery of thioamide in natural protein, methyl-coenzyme M reductase (MCR), raises an important fundamental question of its role in protein conformation and stability. However, the synthesis of thio modified peptides/proteins is challenging. Therefore, we first focused on the synthetic procedure for the synthesis of thioamidated peptides and proteins. We have shown the compatibility of our synthetic method in incorporating the thionated derivative of all the 20 naturally occurring amino acids onto a growing peptide chain. We also report the use of a 2% DBU + 5% piperazine cocktail for fast Fmoc-deprotection that allowed us to synthesize thioamidated Pin1 WW domain and GB1 directly on a solid support. Next, we demonstrated the role of a single n→π* interaction on protein stability by engineering n→π* interaction at the β-turn. Our experimental results at the i+2 residue of type-II’ β-turn in GB1 variants suggest that amino acid side-chain identity and the rotamer conformation can modulate the strength of an n→π* interaction. The altered rotamer conformation as a result of local structural changes within a protein can amplify/weaken an n→π* interaction affecting the backbone torsion angles (phi, psi), and thereby influencing its stability. Further, we amplified the strength of n→π* interaction by replacing i+1 donor carbonyl with thiocarbonyl and validated that the n→π* interaction can indeed influence the structural stability of proteins. We also highlighted the potential impact of a single atom substitution in stabilizing the β-sheet protein. It broadens the scope of this backbone mutation approach in designing/stabilizing the protein scaffold.
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Livres sur le sujet "Synthesis of thioamide"

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Reilly, William Leo 1926. Some Reactions of Fluorocarbon Nitriles : Syntheses of Amidines, Thioamides and Triazines. Creative Media Partners, LLC, 2021.

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Chapitres de livres sur le sujet "Synthesis of thioamide"

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Murai, Toshiaki. « Synthesis of Thioamides ». Dans Chemistry of Thioamides, 45–73. Singapore : Springer Singapore, 2019. http://dx.doi.org/10.1007/978-981-13-7828-7_3.

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Kumagai, Naoya, et Masakatsu Shibasaki. « Asymmetric Synthesis Using Thioamides ». Dans Chemistry of Thioamides, 103–25. Singapore : Springer Singapore, 2019. http://dx.doi.org/10.1007/978-981-13-7828-7_5.

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Yan, Hong, et Hai-Chao Xu. « Synthesis of Heterocycles from Thioamides ». Dans Chemistry of Thioamides, 127–55. Singapore : Springer Singapore, 2019. http://dx.doi.org/10.1007/978-981-13-7828-7_6.

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Zhang, Xue, Jinhua Yang et Junfeng Zhao. « Ynamide-Mediated Synthetic Approach to Thioamide-Substituted Peptides ». Dans Methods in Molecular Biology, 69–80. New York, NY : Springer US, 2022. http://dx.doi.org/10.1007/978-1-0716-2489-0_6.

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Kantlehner, W. « Synthesis from α-Phosphoryl Thioamide Derivatives ». Dans Three Carbon-Heteroatom Bonds : Ketenes and Derivatives, 1. Georg Thieme Verlag KG, 2006. http://dx.doi.org/10.1055/sos-sd-024-00418.

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Chou, Jonathan Chiu-Chun, Veronica E. Stafford, Grace E. Kenney et Laura M. K. Dassama. « The enzymology of oxazolone and thioamide synthesis in methanobactin ». Dans Synthetic and Enzymatic Modifications of the Peptide Backbone, 341–73. Elsevier, 2021. http://dx.doi.org/10.1016/bs.mie.2021.04.008.

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Taber, Douglass F. « Enantioselective Preparation of Alkylated Stereogenic Centers ». Dans Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0042.

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Jon D. Stewart of the University of Florida established (Chem. Commun. 2010, 46, 8558) a scalable enzymatic reduction of geranial 1 to citronellal 2. Andreas S. Bommarius of Georgia Tech reported (Chem. Commun. 2010, 46, 8809) related studies. Isamu Shiina of the Tokyo University of Science developed (J. Am. Chem. Soc. 2010, 132, 11629) a nucleophilic catalyst for the kinetic resolution of α-chiral carboxylic acids such as 3. David W. C. MacMillan of Princeton University devised (J. Am. Chem. Soc. 2010, 132, 13600) a protocol for the enantioselective benzylation of an aldehyde 5. Kian L. Tan of Boston College (J. Am. Chem. Soc. 2010, 132, 14757) and Shannon S. Stahl and Clark R. Landis of the University of Wisconsin (J. Am. Chem. Soc. 2010, 132, 14027) developed the regioselective enantioselective hydroformylation of alkenes such as 7 with chelating substituents. Masaya Sawamura of Hokkaido University (J. Am. Chem. Soc. 2010, 132, 879) and others (Org. Lett. 2010, 12, 2438; Tetrahedron Lett. 2010, 5592, 6018) effected enantiospecific allylic coupling, as in the conversion of 9 to 10 . James P. Morken, also of Boston College, achieved (J. Am. Chem. Soc. 2010, 132, 10686) enantioselective allylation of 11. Ben L. Feringa of the University of Groningen devised (J. Am. Chem. Soc. 2010, 132, 13152) a protocol for net enantioselective conjugate addition to an α, β-unsaturated alde hyde 14. Gary A. Molander of the University of Pennsylvania found (J. Am. Chem. Soc. 2010, 132, 17108) that coupling of 16, prepared by enantioselective conjugate addition, proceeded with inversion. Naoya Kumagai and Masakatsu Shibasaki of the Institute of Microbial Chemistry effected (J. Am. Chem. Soc. 2010, 132, 10275) enantioselective alkynylation of the thioamide 18, and Takahiro Nishimura and Tamio Hayashi of Kyoto University achieved (Chem. Commun. 2010, 46, 6837) conjugate alkynylation of the nitroalkene 20. Several other protocols (Angew. Chem. Int. Ed. 2010, 49, 5780, 7299, 8145; J. Am. Chem. Soc. 2010, 132, 14373; J. Org. Chem. 2010, 75, 7829) have been developed for the catalytic enantioselective construction of arylated stereogenic centers.
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Taber, Douglass F. « Stereocontrolled C-N Ring Construction : The Pyne Synthesis of Hyacinthacine B 3 ». Dans Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0054.

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Keiji Maruoka of Kyoto University found (Organic Lett. 2010, 12, 1668) that the diazo amide 1 derived from the Oppolzer sultam condensed with the imine 2 to give the aziridine 3 with high stereocontrol. Andrei K. Yudin of the University of Toronto observed (Angew. Chem. Int. Ed. 2010, 49, 1607) that the unprotected aziridine aldehyde 4, which exists as a mixture of dimers, condensed smoothly with the Ohira reagent 5 to give the alkynyl aziridine 6. David M. Hodgson of the University of Oxford successfully (Angew. Chem. Int. Ed. 2010, 49, 2900) deprotonated the azetidine thioamide 7 to give, after allylation, the azetidine 8. Varinder K. Aggarwal of the University of Bristol devised (Chem. Commun. 2010, 267) a Pd catalyst for the cyclocarbonylation of an alkenyl aziridine 9 to give the β-lactam 10. Iain Coldham of the University of Sheffield used (J. Org. Chem. 2010, 75, 4069) the ligand they had developed to effect enantioselective allylation of the pyrrolidine derivative 11. The corrresponding piperidine worked as well. John P. Wolfe of the University of Michigan established (Organic Lett. 2010, 12, 2322) that the Pd-mediated cyclization of 13 to 15 could be effected with high diastereocontrol. Christopher G. Frost of the University of Bath optimized (Angew. Chem. Int. Ed. 2010, 49, 1825) the tandem Ru-mediated conjugate addition/cyclization of 16 to give 18 in high ee. Barry M. Trost of Stanford University extended (J. Am. Chem. Soc. 2010, 132, 8238) their studies of trimethylenemethane cycloaddition to the ketimine 19, leading to the substituted pyrrolidine 21 in high ee. Pher G. Andersson of Uppsala University optimized (J. Am. Chem. Soc. 2010, 132, 8880) an Ir catalyst for the enantioselective hydrogenation of readily prepared tetrahydropyridines such as 22. Min Shi of the Shanghai Institute of Organic Chemistry devised (J. Org. Chem. 2010, 75, 3935) a Pd catalyst for enantioselective conjugate addition to the prochiral pyridone 24. Xiaojun Huang of Roche Palo Alto prepared (Tetrahedron Lett. 2010, 51, 1554) the monoacid 26 by enantioselective methanolysis of the anhydride. Selective formylation of the ester led to the pyridone 27.
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Tang, R. Y. « 22.1.7.2 Thioamides (Update 2024) ». Dans Knowledge Updates 2024/1. Stuttgart : Georg Thieme Verlag KG, 2023. http://dx.doi.org/10.1055/sos-sd-122-00021.

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Abstract This is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of thioamides, with a focus on the literature published in the period 2005-2022. In this time, a number of new synthetic methods for the preparation of thioamides have been developed. A variety of substrates, including amides, aldehydes, ketones, nitriles, carboxylic acids, thiocarboxylic acids, β-oxo carboxylic acids, alkynes, alkenes, oximes, benzylamines, benzylic alcohols, benzylic thiols, benzyl disulfides, active methylene compounds, and isothiocyanates have been applied in these transformations. The sulfur agents used include Lawesson’s reagent, elemental sulfur, sulfide salts, phosphorus pentasulfide, thiourea, dithiophosphate, carbon disulfide, and thiophosphoryl chloride.
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Braverman, S., M. Cherkinsky et M. L. Birsa. « Synthesis of Thioamides ». Dans Four Carbon-Heteroatom Bonds, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-018-00203.

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Actes de conférences sur le sujet "Synthesis of thioamide"

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Stojković, Danijela, Maja Đukić, Marija Ristić, Marina Ćendić Serafinović, Svetlana Belošević, Emina Mrkalić et Ivan Jakovljević. « Synthesis, characterization and HSA interactions of a new piano-stool ruthenium(II) complex containing a thioamide-type ligand ». Dans 2nd International Conference on Chemo and Bioinformatics. Institute for Information Technologies, University of Kragujevac, 2023. http://dx.doi.org/10.46793/iccbi23.507s.

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The synthesis and characterization of a newly synthesized piano-stool [Ru-(ɳ6-p-cymene)Cl2L] complex with a ligand 3-amino-2-cyano-N-phenyl-3-(4-phenyl-1-piperazinyl)-2-propenethioamide are presented. The complex was obtained in good yield as an ochre powderand was characterized by elemental analysis, 1H and 13C NMR, IR, conductometry, and melting point. The fluorescence binding studies showed that the interaction of the complex with albumin occurs by a static quenching mechanism and that the complex showed a very high value of the binding constant with one binding site (Kb = 1.68 × 107; n = 1.37). In order to identify the binding location in the HSA molecule, competitive experiments with site markers (eosin Y (site I) and ibuprofen (site II)) were performed. Obtained results showed that the examined complex binds to the site I of subdomain IIA (for eosin Y: Kb = 5.94 × 102; n = 0.65 vs. for ibuprofen: Kb = 1.38 × 107; n= 1.34).
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Dekamin, Mohammad G., Niaz Kheirabi et Zahra Karimi. « A green and facile ultrasound-promoted synthesis of thioamide derivatives catalyzed by Cu(I)@Chitosan as a new bio-polymeric nano catalyst in aqueous media ». Dans The 19th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland : MDPI, 2015. http://dx.doi.org/10.3390/ecsoc-19-a028.

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Dotsenko, Victor, Konstantin Frolov et Sergey Krivokolysko. « DMSO-HCl System as an Efficient Oxidant of Thioamides and Selenoamides ». Dans The 16th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland : MDPI, 2012. http://dx.doi.org/10.3390/ecsoc-16-01073.

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Levchenko, Arina G., Polina G. Dahno et Victor V. Dotsenko. « Synthesis of N-(hydroxymethylene)thioamides by N-hydroxymethylation of 2-cyanothioacrylamides ». Dans ECSOC-25. Basel Switzerland : MDPI, 2021. http://dx.doi.org/10.3390/ecsoc-25-11799.

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Heimgartner, Heinz, Jürg Lehmann et Anthony Linden. « Site-Selective Incorporation of Thioamide-Linkages into a Growing Peptide via Variation of the 'Azirine/Oxazolone Method' ». Dans The 1st International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland : MDPI, 1997. http://dx.doi.org/10.3390/ecsoc-1-02033.

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Muntyan, Victoria S., Mariia E. Vladimirova, Alexey M. Afonin, Alexey N. Muntyan et Marina L. Roumiantseva. « ANALYSIS OF SALT-SENSITIVE AND SALT-TOLERANT SINORHIZOBIUM MELILOTI STRAINS USING DNA MICROARRAY, PHENOTYPE MICROARRAY AND GENOME MINING TECHNIQUES ». Dans 23rd SGEM International Multidisciplinary Scientific GeoConference 2023. STEF92 Technology, 2023. http://dx.doi.org/10.5593/sgem2023/6.1/s25.15.

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Nodule bacteria increase the resistance of host plants to abiotic stress factors; however, the role of the genetic potential of rhizobia in the formation of productive salt-tolerant plant-microbial symbiosis remains underestimated. The aim of the study was to evaluate the pool of genes responsible for the salt tolerance of the alfalfa microsymbiont, Sinorhizobium meliloti, using the DNA microarray technique, phenotype microarray (PM), NGS and NNGS-technologies and genome mining (antismash 5.0). As a result of the analysis of the genomes of strains contrastingly different in salt tolerance, it was found that nucleotide changes in genes in salt-sensitive strains occurred significantly more often in genomic islands located on the chromosome. The genome of the salttolerant strain contained at least 25 genes involved in the DNA replication and repair and metabolism of nucleotides (1 KEGG group), amino acids (8 KEGG groups), lipids (2 KEGG groups), and carbohydrates (4 KEGG groups). Genomic analysis of the saltsensitive strain revealed 2 unique secondary metabolite biosynthesis gene clusters on pSymB (NAGGN) and on the cryptic plasmid (phosphonate and ectoine), while both gene clusters are involved in the synthesis of substances that involved in osmotic stress response. In the genomes of salt-tolerant phenotype strains, changes occurred in a smaller number of genes belonging to other KEGG groups. Two unique clusters of antibiotic synthesis, the class of macrolides (conglobactin) and aminoglycosides (2- deoxystreptamine), as well as an additional cluster of synthesis of thioamitide RiPPs, were identified on the chromosome of a salt-tolerant strain using genome mining. The use of the PM technique made it possible to show that the salt-tolerant strain is resistant to 10 beta-lactam antibiotics, 7 cephalosporins, 9 aminoglycoside antibiotics, 5 tetracyclines, polymyxin E, and 16 antibiotics that block the synthesis of DNA, RNA, enzymes and proteins, while the salt-sensitive strain grew up on alternative sources of organic sulfur and carbon. The revealed characteristics of strains that contrastingly differ in stress tolerance are promising for their use in agrobiotechnology.
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