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Journal articles on the topic 'Allylamides'

Author: Grafiati

Published: 23 November 2024

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1

Krompiec, Stanisław, Mariola Pigulla, Michał Krompiec, Stefan Baj, Julita Mrowiec-Białoń, and Janusz Kasperczyk. "Highly selective isomerization of N-allylamides and N-allylamines." Tetrahedron Letters 45, no. 27 (June 2004): 5257–61. http://dx.doi.org/10.1016/j.tetlet.2004.05.023.

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2

Chiacchio, Ugo, Gianluigi Broggini, Roberto Romeo, Silvia Gazzola, Maria A. Chiacchio, Salvatore V. Giofrè, Bartolo Gabriele, Raffaella Mancuso, Giuseppe Floresta, and Chiara Zagni. "Intramolecular oxidative palladium-catalyzed diamination reactions of alkenyl sulfamates: an efficient synthesis of [1,2,5]thiadiazolo-fused piperazinones." RSC Advances 6, no. 62 (2016): 57521–29. http://dx.doi.org/10.1039/c6ra13141g.

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3

Ranjith, Jala, Nomula Rajesh, Balasubramanian Sridhar, and Palakodety Radha Krishna. "Intramolecular oxyacetoxylation of N-allylamides: an expeditious synthesis of oxazolines and oxazines by using a PhI(OAc)2/hydrogen fluoride–pyridine system." Organic & Biomolecular Chemistry 14, no. 42 (2016): 10074–79. http://dx.doi.org/10.1039/c6ob01752e.

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4

Deng, Qiao-Hui, Jia-Rong Chen, Qiang Wei, Quan-Qing Zhao, Liang-Qiu Lu, and Wen-Jing Xiao. "Visible-light-induced photocatalytic oxytrifluoromethylation of N-allylamides for the synthesis of CF3-containing oxazolines and benzoxazines." Chem. Commun. 51, no. 17 (2015): 3537–40. http://dx.doi.org/10.1039/c4cc10217g.

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A visible-light-induced photocatalytic oxytrifluoro-methylation reaction of N-allylamides has been described for the efficient synthesis of CF₃-containing oxazolines and benzoxazines in generally high yields.

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5

Chen, Zhichao, Hong Zhang, Shu-Feng Zhou, and Xiuling Cui. "Photoredox-catalyzed synthesis of sulfonated oxazolines from N-allylamides through the insertion of sulfur dioxide." Organic Chemistry Frontiers 9, no. 2 (2022): 364–69. http://dx.doi.org/10.1039/d1qo01540k.

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Photoredox-catalyzed generation of sulfonated oxazolines starting from N-allylamides, DABCO·(SO2)2, and aryldiazonium salts has been developed and a range of sulfonated oxazolines were obtained in moderate to good yields.

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6

Neugnot, Benjamin, Jean-Christophe Cintrat, and Bernard Rousseau. "A new highly chemoselective isomerization of allylamides." Tetrahedron 60, no. 16 (April 2004): 3575–79. http://dx.doi.org/10.1016/j.tet.2004.03.004.

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7

Krainova, G. F., I. A. Tolmacheva, M. N. Gorbunova, and V. V. Grishko. "Synthesis of lupane and a-secolupane allylamides." Chemistry of Natural Compounds 49, no. 2 (May 2013): 281–85. http://dx.doi.org/10.1007/s10600-013-0582-4.

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8

Wylie, Luke, Matthew Flynn, Victoria L. Blair, Philip C. Andrews, and Ekaterina I. Izgorodina. "Isomers of Alkali Metal (Methylbenzyl)allylamides: A Theoretical Perspective." ACS Omega 5, no. 16 (April 13, 2020): 9448–57. http://dx.doi.org/10.1021/acsomega.0c00652.

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9

Moon, Nicholas G., and Andrew M. Harned. "Iodine(III)-promoted synthesis of oxazolines from N-allylamides." Tetrahedron Letters 54, no. 23 (June 2013): 2960–63. http://dx.doi.org/10.1016/j.tetlet.2013.03.140.

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10

Chiusoli, Gian Paolo, Mirco Costa, and Fausto Pivetti. "Rhodium-catalyzed coupling of N-allylamides of organic acids." Journal of Organometallic Chemistry 373, no. 3 (September 1989): 385–89. http://dx.doi.org/10.1016/0022-328x(89)85067-3.

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11

Fu, Hua, Jipan Yu, Hua Tian, Chang Gao, Haijun Yang, and Yuyang Jiang. "Boron-Catalyzed Arylthiooxygenation of N-Allylamides: Synthesis of (Arylsulfanyl)oxazolines." Synlett 26, no. 05 (January 8, 2015): 676–80. http://dx.doi.org/10.1055/s-0034-1378948.

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12

Ojima, Iwao, and Zhaoda Zhang. "Novel amide-directed hydrocarbonylations and double carbonylation of N-allylamides." Journal of Organic Chemistry 53, no. 18 (September 1988): 4422–25. http://dx.doi.org/10.1021/jo00253a051.

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13

Gorbunova, M. N., G. F. Krainova, I. A. Tolmacheva, and V. V. Grishko. "Synthesis of new biologically active polymer bioconjugates based on lupane allylamides." Russian Journal of Bioorganic Chemistry 41, no. 7 (November 27, 2015): 732–38. http://dx.doi.org/10.1134/s1068162015070043.

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14

Hesse, Manfred, and Sergey Sergeyev. "A New Convenient Method for the Preparation of Enamides fromN-Allylamides." Synlett, no. 8 (2002): 1313–17. http://dx.doi.org/10.1055/s-2002-32962.

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15

Moon, Nicholas G., and Andrew M. Harned. "ChemInform Abstract: Iodine(III)-Promoted Synthesis of Oxazolines from N-Allylamides." ChemInform 44, no. 37 (August 22, 2013): no. http://dx.doi.org/10.1002/chin.201337115.

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16

Halli, Juliette, Philipp Kramer, Maren Bechthold, and Georg Manolikakes. "Nickel-Catalyzed Synthesis of Enamides and EnecarbamatesviaIsomerization of Allylamides and Allylcarbamates." Advanced Synthesis & Catalysis 357, no. 14-15 (September 25, 2015): 3321–24. http://dx.doi.org/10.1002/adsc.201500461.

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17

Krompiec, Stanisław, Mariola Pigulla, Nikodem Kuźnik, Michał Krompiec, Bogdan Marciniec, Dariusz Chadyniak, and Janusz Kasperczyk. "Highly selective isomerization of N-allylamides catalyzed by ruthenium and rhodium complexes." Journal of Molecular Catalysis A: Chemical 225, no. 1 (January 2005): 91–101. http://dx.doi.org/10.1016/j.molcata.2004.09.001.

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18

Mukhopadhyay, Manoj, and Javed Iqbal. "Co(III)DMG-Catalyzed Synthesis of Allylamides from Allyl Alcohols and Acetonitrile." Journal of Organic Chemistry 62, no. 6 (March 1997): 1843–45. http://dx.doi.org/10.1021/jo960557q.

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19

Wang, Lu, Chao Liu, Ruopeng Bai, Yani Pan, and Aiwen Lei. "Easy access to enamides: a mild nickel-catalysed alkene isomerization of allylamides." Chemical Communications 49, no. 72 (2013): 7923. http://dx.doi.org/10.1039/c3cc43875a.

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20

Prati, Fabio, Alberto Spaggiari, Daniele Vaccari, and Paolo Davoli. "The Triphenyl Phosphite-Chlorine Reagent in the Synthesis of Pyrroles fromN-Allylamides." Synthesis, no. 6 (2006): 995–98. http://dx.doi.org/10.1055/s-2006-926365.

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21

Yu, Jipan, Hua Tian, Chang Gao, Haijun Yang, Yuyang Jiang, and Hua Fu. "ChemInform Abstract: Boron-Catalyzed Arylthiooxygenation of N-Allylamides: Synthesis of (Arylsulfanyl)oxazolines." ChemInform 46, no. 30 (July 2015): no. http://dx.doi.org/10.1002/chin.201530179.

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22

Matsumoto, Kouichi, Jun-ichi Yoshida, Yu Miyamoto, Naoya Mitani, Rina Yanagi, Shigenori Kashimura, and Seiji Suga. "Synthesis of Oxazolines from N-Allylamides Using an Electrochemically Generated ArS(ArSSAr)+ Pool." HETEROCYCLES 96, no. 8 (2018): 1373. http://dx.doi.org/10.3987/com-18-13942.

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23

Yang, Chun-Hua, Zhong-Qi Xu, Lili Duan, and Yue-Ming Li. "CuBr 2 -promoted intramolecular bromocyclization of N-allylamides and aryl allyl ketone oximes." Tetrahedron 73, no. 48 (November 2017): 6747–53. http://dx.doi.org/10.1016/j.tet.2017.10.025.

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24

Walters, Michael A., Colleen S. McDonough, Perry S. Brown, and Andrew B. Hoem. "An extremely mild 3-aza-Claisen reaction. 1. Rearrangement of simple N-allylamides." Tetrahedron Letters 32, no. 2 (January 1991): 179–82. http://dx.doi.org/10.1016/0040-4039(91)80848-z.

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25

Hilt, Gerhard, Felicia Weber, Philipp Steinlandt, and Monika Ballmann. "Structure-Dependent Nickel-Catalysed Transposition of N-Allylamides to E- or Z-Enamides." Synthesis 49, no. 02 (November 14, 2016): 440–50. http://dx.doi.org/10.1055/s-0036-1588340.

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26

Hu, Yancheng, Xincheng Li, and Boshun Wan. "NIS-mediated ring-closure/opening cascade reactions of allylamides: an expedient route to oxazolines." Tetrahedron 71, no. 38 (September 2015): 6935–43. http://dx.doi.org/10.1016/j.tet.2015.07.011.

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27

Yu, Jipan, Haijun Yang, and Hua Fu. "Transition Metal-Free Trifluoromethylation ofN-Allylamides with Sodium Trifluoromethanesulfinate: Synthesis of Trifluoromethyl-Containing Oxazolines." Advanced Synthesis & Catalysis 356, no. 17 (November 5, 2014): 3669–75. http://dx.doi.org/10.1002/adsc.201400144.

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28

Zhang, Xiaowei, Bonan Cao, Shichao Yu, and Xumu Zhang. "Rhodium-Catalyzed Asymmetric Hydroformylation of N-Allylamides: Highly Enantioselective Approach to β2-Amino Aldehydes." Angewandte Chemie International Edition 49, no. 24 (April 29, 2010): 4047–50. http://dx.doi.org/10.1002/anie.201000955.

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29

Zhang, Xiaowei, Bonan Cao, Shichao Yu, and Xumu Zhang. "Rhodium-Catalyzed Asymmetric Hydroformylation of N-Allylamides: Highly Enantioselective Approach to β2-Amino Aldehydes." Angewandte Chemie 122, no. 24 (April 29, 2010): 4141–44. http://dx.doi.org/10.1002/ange.201000955.

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30

MUKHOPADHYAY, M., and J. IQBAL. "ChemInform Abstract: Co(III)DMG-Catalyzed Synthesis of Allylamides from Allyl Alcohols and Acetonitrile." ChemInform 28, no. 30 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199730070.

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31

Wang, Lu, Chao Liu, Ruopeng Bai, Yani Pan, and Aiwen Lei. "ChemInform Abstract: Easy Access to Enamides: A Mild Nickel-Catalyzed Alkene Isomerization of Allylamides." ChemInform 45, no. 2 (December 19, 2013): no. http://dx.doi.org/10.1002/chin.201402073.

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32

Sergeyev, Sergey, and Manfred Hesse. "ChemInform Abstract: A New Convenient Method for the Preparation of Enamides from N-Allylamides." ChemInform 33, no. 45 (May 19, 2010): no. http://dx.doi.org/10.1002/chin.200245083.

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33

Ghannoum, Mahmoud. "Azole Resistance in Dermatophytes." Journal of the American Podiatric Medical Association 106, no. 1 (January 1, 2016): 79–86. http://dx.doi.org/10.7547/14-109.

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Azole antifungal agents (eg, fluconazole and itraconazole) have been widely used to treat superficial fungal infections caused by dermatophytes and, unlike the allylamines (such as terbinafine and naftifine), have been associated with resistance development. Although many published manuscripts describe resistance to azoles among yeast and molds, reports describing resistance of dermatophytes are starting to appear. In this review, I discuss the mode of action of azole antifungals and mechanisms underlying their resistance compared with the allylamine class of compounds. Data from published and original studies were compared and summarized, and their clinical implications are discussed. In contrast to the cidal allylamines, static drugs such as azoles permit the occurrence of mutations in enzymes involved in ergosterol biosynthesis, and the ergosterol precursors accumulating as a consequence of azole action are not toxic. Azole antifungals, unlike allylamines, potentiate resistance development in dermatophytes.

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34

Bezemer, Jacob M., Jacob van der Ende, Jacqueline Limpens, Henry J. C. de Vries, and Henk D. F. H. Schallig. "Safety and efficacy of allylamines in the treatment of cutaneous and mucocutaneous leishmaniasis: A systematic review." PLOS ONE 16, no. 4 (April 7, 2021): e0249628. http://dx.doi.org/10.1371/journal.pone.0249628.

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Cutaneous and mucocutaneous leishmaniasis affect a million people yearly, leading to skin lesions and potentially disfiguring mucosal disease. Current treatments can have severe side effects. Allylamine drugs, like terbinafine, are safe, including during pregnancy. This review assesses efficacy and safety of allylamines for the treatment of cutaneous and mucocutaneous leishmaniasis. It followed the PRISMA statement for reporting and was preregistered in PROSPERO(CRD4201809068). MEDLINE, EMBASE, the Cochrane Central Register of Controlled Trials, the Global Health Library, Web of Science, Google Scholar, and clinical trial registers were searched from their creation to May 24th, 2020. All original human, animal, and in vitro studies concerning allylamines and cutaneous or mucocutaneous leishmaniasis were eligible for inclusion. Comparators—if any—included both placebo or alternative cutaneous or mucocutaneous leishmaniasis treatments. Complete cure, growth inhibition, or adverse events served as outcomes. The search identified 312 publications, of which 22 were included in this systematic review. There were one uncontrolled and two randomised controlled trials. The only well-designed randomised controlled trial that compared the treatment efficacy of oral terbinafine versus intramuscular meglumine antimoniate in 80 Leismania tropica infected patients showed a non-significant lower cure rate for terbinafine vs meglumine antimoniate (38% vs 53%). A meta-analysis could not be performed due to the small number of studies, their heterogeneity, and low quality. This systematic review shows that there is no evidence of efficacy of allylamine monotherapy against cutaneous and mucocutaneous leishmaniasis. Further trials of allylamines should be carefully considered as the outcomes of an adequately designed trial were disappointing and in vitro studies indicate minimal effective concentrations that are not achieved in the skin during standard doses. However, the in vitro synergistic effects of allylamines combined with triazole drugs warrant further exploration.

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35

Chiba, Shunsuke, Line Zhang, Jian-Yuan Lee, and Naomi Yamazaki. "Copper(II)-Catalyzed Synthesis of Pyrazinones from α-Azido-N-allylamides under an Oxygen Atmosphere." Synlett 2011, no. 15 (August 12, 2011): 2167–70. http://dx.doi.org/10.1055/s-0030-1261185.

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36

Halli, Juliette, Philipp Kramer, Maren Bechthold, and Georg Manolikakes. "ChemInform Abstract: Nickel-Catalyzed Synthesis of Enamides and Enecarbamates via Isomerization of Allylamides and Allylcarbamates." ChemInform 47, no. 9 (February 2016): no. http://dx.doi.org/10.1002/chin.201609020.

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37

Klychnikov, Mikhail K., Radek Pohl, Ivana Císařová, and Ullrich Jahn. "α,γ-Dioxygenated amides via tandem Brook rearrangement/radical oxygenation reactions and their application to syntheses of γ-lactams." Beilstein Journal of Organic Chemistry 17 (March 9, 2021): 688–704. http://dx.doi.org/10.3762/bjoc.17.58.

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Pyrrolidones are common heterocyclic fragments in various biologically active compounds. Here, a two-step radical-based approach to γ-lactams bearing three to four stereocenters starting from epoxides, N-allylic silylacetamides and TEMPO is reported. The sequence starts with a new tandem nucleophilic substitution/Brook rearrangement/single electron transfer-induced radical oxygenation furnishing orthogonally protected α,γ-dioxygenated N-allylamides with wide scope, mostly good yields, and partly good diastereo- and enantioselectivity for defined combinations of chiral epoxides and chiral amides. This represents a very rare example of an oxidative geminal C–C/C–O difunctionalization next to carbonyl groups. The resulting dioxygenated allylic amides are subsequently subjected to persistent radical effect-based 5-exo-trig radical cyclization reactions providing functionalized pyrrolidones in high yields as diastereomeric mixtures. They converge to 3,4-trans-γ-lactams by base-mediated equilibration, which can be easily further diversified. Stereochemical models for both reaction types were developed.

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38

Ueda, Kazutaka, and Miwako Mori. "Synthesis of allylamides from allyl halides, carbon monoxide, and titanium–nitrogen complexes prepared from molecular nitrogen." Tetrahedron Letters 45, no. 14 (March 2004): 2907–10. http://dx.doi.org/10.1016/j.tetlet.2004.02.072.

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39

Zhang, Xiaowei, Bonan Cao, Shichao Yu, and Xumu Zhang. "ChemInform Abstract: Rhodium-Catalyzed Asymmetric Hydroformylation of N-Allylamides: Highly Enantioselective Approach to β2-Amino Aldehydes." ChemInform 41, no. 38 (August 26, 2010): no. http://dx.doi.org/10.1002/chin.201038044.

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40

Broggini, Gianluigi, Egle M. Beccalli, Tea Borelli, Filippo Brusa, Silvia Gazzola, and Alberto Mazza. "Intra-Intermolecular Palladium-Catalyzed Domino Reactions of Glycine Allylamides for the Synthesis of Diversely Functionalized Piperazinones." European Journal of Organic Chemistry 2015, no. 19 (May 27, 2015): 4261–68. http://dx.doi.org/10.1002/ejoc.201500386.

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41

Akssira, Mohamed, Farid El Guemmout, Patrick Bauchat, and André Foucaud. "Synthèses de diallylamines et triallylamines à partir des 3-acetoxy-3-aryl-2-méthylène propionitriles et des 3-acétoxy-3-aryl-2-méthylène propionates de méthyle." Canadian Journal of Chemistry 72, no. 5 (May 1, 1994): 1357–61. http://dx.doi.org/10.1139/v94-169.

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The reactions of 3-acetoxy-3-aryl-2-methylene propionitriles 1 with ammonia yielded the corresponding diallylamines 3ZZ. The reaction of 1 with a primary allylamine or with ethylene diamine gave the diallylamine 11 or 13ZZ. The treatment of methyl 3-acetoxy-3-aryl-2-methylene propionates 2 with isopropylamine or ethylene diamine gave the allylamines 6EE or 14 and 15, but the reaction of 2 with ammonia gave only the triallylamines 4EEE in good yields.

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42

Li, Yali, Lingjuan Zhang, Zongyao Zhang, Jianbin Xu, Yixiao Pan, Conghui Xu, Lingxian Liu, et al. "Regio- and Stereoselective Synthesis of 1,2,3-Trisubstituted Indanes from Diarylmethanols and Allylamides through Iron(III) Chloride Hexahydrate." Advanced Synthesis & Catalysis 358, no. 13 (June 16, 2016): 2148–55. http://dx.doi.org/10.1002/adsc.201600165.

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43

Zhang, Line, Jian-Yuan Lee, Naomi Yamazaki, and Shunsuke Chiba. "ChemInform Abstract: Copper(II)-Catalyzed Synthesis of Pyrazinones from α-Azido-N-allylamides under an Oxygen Atmosphere." ChemInform 43, no. 5 (January 5, 2012): no. http://dx.doi.org/10.1002/chin.201205199.

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44

Yu, Jipan, Haijun Yang, and Hua Fu. "ChemInform Abstract: Transition Metal-Free Trifluoromethylation of N-Allylamides with Sodium Trifluoromethanesulfinate: Synthesis of Trifluoromethyl-Containing Oxazolines." ChemInform 46, no. 18 (April 16, 2015): no. http://dx.doi.org/10.1002/chin.201518154.

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45

Broggini, Gianluigi, Egle M. Beccalli, Tea Borelli, Filippo Brusa, Silvia Gazzola, and Alberto Mazza. "ChemInform Abstract: Intra-Intermolecular Palladium-Catalyzed Domino Reactions of Glycine Allylamides for the Synthesis of Diversely Functionalized Piperazinones." ChemInform 46, no. 45 (October 22, 2015): no. http://dx.doi.org/10.1002/chin.201545184.

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46

Deng, Qiao-Hui, Jia-Rong Chen, Qiang Wei, Quan-Qing Zhao, Liang-Qiu Lu, and Wen-Jing Xiao. "ChemInform Abstract: Visible-Light-Induced Photocatalytic Oxytrifluoromethylation of N-Allylamides for the Synthesis of CF3-Containing Oxazolines and Benzoxazines." ChemInform 46, no. 28 (June 25, 2015): no. http://dx.doi.org/10.1002/chin.201528171.

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47

Kawamura, Shintaro, Daisuke Sekine, and Mikiko Sodeoka. "Synthesis of CF3-containing oxazolines via trifluoromethylation of allylamides with Togni reagent in the presence of alkali metal iodides." Journal of Fluorine Chemistry 203 (November 2017): 115–21. http://dx.doi.org/10.1016/j.jfluchem.2017.07.012.

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48

Thiedemann, Birk, Christin M. L. Schmitz, and Anne Staubitz. "Reduction of N-Allylamides by LiAlH4: Unexpected Attack of the Double Bond with Mechanistic Studies of Product and Byproduct Formation." Journal of Organic Chemistry 79, no. 21 (October 27, 2014): 10284–95. http://dx.doi.org/10.1021/jo501907v.

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49

Broggini, Gianluigi, Vincenzina Barbera, Egle M. Beccalli, Elena Borsini, Simona Galli, Giuseppe Lanza, and Gaetano Zecchi. "Palladium(II)/Copper Halide/Solvent Combination for Selective Intramolecular Domino Reactions of Indolecarboxylic Acid Allylamides: An Unprecedented Arylation/Esterification Sequence." Advanced Synthesis & Catalysis 354, no. 1 (January 2012): 159–70. http://dx.doi.org/10.1002/adsc.201100614.

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50

Li, Yutian, Li Wang, Shengbin Zhou, Guoxue He, and Yu Zhou. "Electrochemical oxidative cyclization of N-allylamides for the synthesis of CF₃-containing benzoxazines and oxazolines." RSC Advances 14, no. 1 (2024): 154–59. http://dx.doi.org/10.1039/d3ra07282g.

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