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Автор: Grafiati

Опубліковано: 6 вересня 2023

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1

Chamberlain, Anna E. R., Kieran J. Paterson, Roly J. Armstrong, Heather C. Twin, and Timothy J. Donohoe. "A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles." Chemical Communications 56, no. 24 (2020): 3563–66. http://dx.doi.org/10.1039/d0cc00903b.

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2

Rulev, A. Yu, and A. R. Romanov. "Unsaturated polyfluoroalkyl ketones in the synthesis of nitrogen-bearing heterocycles." RSC Advances 6, no. 3 (2016): 1984–98. http://dx.doi.org/10.1039/c5ra23759a.

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3

Zonker, Benjamin, Ediz Duman, Heike Hausmann, Jonathan Becker, and Radim Hrdina. "[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold." Organic & Biomolecular Chemistry 18, no. 26 (2020): 4941–45. http://dx.doi.org/10.1039/d0ob01156h.

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4

Singh, Deepak, and Hyun-Joon Ha. "Metal-free aza-Claisen type ring expansion of vinyl aziridines: an expeditious synthesis of seven membered N-heterocycles." Organic & Biomolecular Chemistry 17, no. 12 (2019): 3093–97. http://dx.doi.org/10.1039/c8ob03029d.

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5

Frontier, Alison J., Shukree Abdul-Rashed, and Connor Holt. "Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications." Synthesis 52, no. 14 (April 9, 2020): 1991–2007. http://dx.doi.org/10.1055/s-0039-1690869.

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Анотація:

This review focuses on alkynyl Prins and alkynyl aza-Prins cyclization processes, which involve intramolecular coupling of an alkyne with either an oxocarbenium or iminium electrophile. The oxocarbenium or iminium species can be generated through condensation- or elimination-type processes, to achieve an overall bimolecular annulation that enables the synthesis of both oxygen- and nitrogen-containing saturated heterocycles with different ring sizes and substitution patterns. Also discussed are cascade processes in which alkynyl Prins heterocyclic adducts react to trigger subsequent pericyclic reactions, including [4+2] cycloadditions and Nazarov electrocyclizations, to rapidly construct complex small molecules. Finally, examples of the use of alkynyl Prins and alkynyl aza-Prins reactions in the synthesis of natural products are described. The review covers the literature through the end of 2019.1 Introduction1.1 Alkyne-Carbonyl Coupling Pathways1.2 Coupling/Cyclization Cascades Using the Alkynyl Prins Reaction2 Alkynyl Prins Annulation (Oxocarbenium Electrophiles)2.1 Early Work2.2 Halide as Terminal Nucleophile2.3 Oxygen as Terminal Nucleophile2.4 Arene as Terminal Nucleophile (Intermolecular)2.5 Arene Terminal Nucleophile (Intramolecular)2.6 Cyclizations Terminated by Elimination3 Synthetic Utility of Alkynyl Prins Annulation3.1 Alkynyl Prins-Mediated Synthesis of Dienes for a [4+2] Cyclo- addition-Oxidation Sequence3.2 Alkynyl Prins Cyclization Adducts as Nazarov Cyclization Precursors3.3 Alkynyl Prins Cyclization in Natural Product Synthesis4 Alkynyl Aza-Prins Annulation4.1 Iminium Electrophiles4.2 Activated Iminium Electrophiles5 Alkynyl Aza-Prins Cyclizations in Natural Product Synthesis6 Summary and Outlook

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6

Gusar, N. I. "Synthesis of heterocycles by the aza-Wittig reaction." Russian Chemical Reviews 60, no. 2 (February 28, 1991): 146–61. http://dx.doi.org/10.1070/rc1991v060n02abeh001036.

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7

Yang, Xu-Heng, Jian Huang, Fang Wang, Zhuoliang Liu, Yujiao Li, Cheng-an Tao, and Jianfang Wang. "Copper-catalyzed alkynylation/annulation cascades of N-allyl ynamides: regioselective access to medium-sized N-heterocycles." Organic Chemistry Frontiers 8, no. 1 (2021): 18–24. http://dx.doi.org/10.1039/d0qo00837k.

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Анотація:

A synthetic strategy based on sequential application of aza-Claisen rearrangement, C–H functionalization, C–N coupling and cyclization as key steps has been developed for the synthesis of 6-, 7-, 8-, and 9-membered rings N-heterocycles.

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8

Guin, Soumitra, Debashis Majee, and Sampak Samanta. "Unmasking the reverse reactivity of cyclic N-sulfonyl ketimines: multifaceted applications in organic synthesis." Chemical Communications 57, no. 72 (2021): 9010–28. http://dx.doi.org/10.1039/d1cc03439a.

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Анотація:

This feature article covers the recent status on the reactivities of α-alkyl cyclic N-sulfonyl ketimines as resourceful nucleophiles, targeting fused carbo- and heterocycles, aza-arenes etc. In addition, the mechanistic studies have been presented.

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9

Seath, Ciaran P., Kirsty L. Wilson, Angus Campbell, Jenna M. Mowat, and Allan J. B. Watson. "Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(i)/Pd(0)/Cu(ii) cascade catalysis of 2-iodoaniline/phenols." Chemical Communications 52, no. 56 (2016): 8703–6. http://dx.doi.org/10.1039/c6cc04554e.

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Анотація:

A one-pot cascade reaction for the synthesis of 2-BMIDA 6,5-bicyclic heterocycles has been developed using Cu(i)/Pd(0)/Cu(ii) catalysis. The method provides efficient access to borylated indoles, benzofurans, and aza-derivatives, which can be difficult to access through alternative methods.

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10

Nguyen, Thi Thu Tram, Le Anh Nguyen, Quoc Anh Ngo, Marina Koleski, and Thanh Binh Nguyen. "The catalytic role of elemental sulfur in the DMSO-promoted oxidative coupling of methylhetarenes with amines: synthesis of thioamides and bis-aza-heterocycles." Organic Chemistry Frontiers 8, no. 7 (2021): 1593–98. http://dx.doi.org/10.1039/d0qo01654c.

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11

Zhang, Yong-Sheng, Xiang-Ying Tang, and Min Shi. "Unprecedented synthesis of aza-bridged benzodioxepine derivatives through a tandem Rh(ii)-catalyzed 1,3-rearrangement/[3+2] cycloaddition of carbonyltriazoles." Chem. Commun. 50, no. 100 (2014): 15971–74. http://dx.doi.org/10.1039/c4cc08339c.

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Анотація:

Rh(ii)-catalyzed novel tandem intramolecular cycloisomerizations of aldehydes or ketones with 1-sulfonyl 1,2,3-triazoles have been disclosed, providing a facile protocol to access a series of functionalized aza-bridged benzodioxepine heterocycles.

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12

Wang, Yan-Yan, Tuan-Jie Wang, Juan Chen, Chao-Yang Wang, and Jing Zhu. "Synthesis of Polycationic Aza-Belted Heterocyclic Iodomethane Salts." Advanced Science, Engineering and Medicine 11, no. 11 (November 1, 2019): 1134–41. http://dx.doi.org/10.1166/asem.2019.2468.

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Анотація:

Novel belt shapes of a diazabicyclo[n,n,5.5]alkane center combined with double iodomethane salts were prepared in two steps by a reaction of phenylethylamine or 3,4-dimethoxyphenylethylamine with ortho-bis(chloromethyl)benzenes. The syntheses and characteristics of these polycationic systems containing aza-belt rings are described. Judicious choice of the reaction conditions allowed these polycationic heterocycles to be generated in good yields, and 1H and 13C nuclear magnetic resonance spectroscopy revealed a change in chemical shifts caused by interactions between the functional groups.

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13

Nayl, AbdElAziz A., Ashraf A. Aly, Wael A. A. Arafa, Ismail M. Ahmed, Ahmed I. Abd-Elhamid, Esmail M. El-Fakharany, Mohamed A. Abdelgawad, Hendawy N. Tawfeek, and Stefan Bräse. "Azides in the Synthesis of Various Heterocycles." Molecules 27, no. 12 (June 9, 2022): 3716. http://dx.doi.org/10.3390/molecules27123716.

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Анотація:

In this review, we focus on some interesting and recent examples of various applications of organic azides such as their intermolecular or intramolecular, under thermal, catalyzed, or noncatalyzed reaction conditions. The aforementioned reactions in the aim to prepare basic five-, six-, organometallic heterocyclic-membered systems and/or their fused analogs. This review article also provides a report on the developed methods describing the synthesis of various heterocycles from organic azides, especially those reported in recent papers (till 2020). At the outset, this review groups the synthetic methods of organic azides into different categories. Secondly, the review deals with the functionality of the azido group in chemical reactions. This is followed by a major section on the following: (1) the synthetic tools of various heterocycles from the corresponding organic azides by one-pot domino reaction; (2) the utility of the chosen catalysts in the chemoselectivity favoring C−H and C-N bonds; (3) one-pot procedures (i.e., Ugi four-component reaction); (4) nucleophilic addition, such as Aza-Michael addition; (5) cycloaddition reactions, such as [3+2] cycloaddition; (6) mixed addition/cyclization/oxygen; and (7) insertion reaction of C-H amination. The review also includes the synthetic procedures of fused heterocycles, such as quinazoline derivatives and organometal heterocycles (i.e., phosphorus-, boron- and aluminum-containing heterocycles). Due to many references that have dealt with the reactions of azides in heterocyclic synthesis (currently more than 32,000), we selected according to generality and timeliness. This is considered a recent review that focuses on selected interesting examples of various heterocycles from the mechanistic aspects of organic azides.

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14

Balci, Metin. "Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles." Synthesis 50, no. 07 (February 1, 2018): 1373–401. http://dx.doi.org/10.1055/s-0036-1589527.

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Carbon–nitrogen bond formation is one of the most important reactions in organic chemistry. Various synthetic strategies for the generation of C–N bonds are described in the literature. For example, primary amines can be easily synthesized by the thermal decomposition of an acyl azide to an isocyanate, i.e. the Curtis rearrangement, followed by hydrolysis; the Curtius rearrangement has been used extensively. Furthermore, the advantage of the Curtius rearrangement is the isolation of acyl azides as well as the corresponding isocyanates. The isocyanates can be converted into various nitrogen-containing compounds upon reaction with various nucleophiles that can be used as important synthons for cyclization, in other words, for the synthesis of heterocycles. Therefore, this review demonstrates the importance of acyl azides not only in the synthesis acyclic systems, but also in the synthesis of various nitrogen-containing heterocycles.1 Introduction2 Synthesis of Acyl Azides2.1 Acyl Azides from Carboxylic Acid Derivatives2.2 Acyl Azides by Direct Transformation of Carboxylic Acids2.3 Acyl Azides from Aldehydes2.4 Carbamoyl Azides from Haloarenes, Sodium Azide, and N-Formylsaccharin3 Mechanism of Formation of Isocyanates4 Synthesis of Diacyl Azides5 Synthetic Applications5.1 Synthesis of Pyrimidinone Derivatives5.2 Dihydropyrimidinone and Isoquinolinone Derivatives5.3 Synthesis of Tetrahydroisoquinoline Skeleton5.4 Synthesis of Five-Membered Heterocycles5.5 Heterocycles Synthesized Starting from Homophthalic acid5.6 Heterocycles Synthesized from 2-(Ethoxycarbonyl)nicotinic Acid5.7 Formation of Aza-spiro Compounds5.8 Parham-Type Cyclization5.9 Diazepinone Derivatives5.10 Synthesis of Pyridine Derivatives5.11 Synthesis of Indole Derivatives6 Miscellaneous7 Conclusion

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15

Heredia-Moya, Jorge, Daniel A. Zurita, José Eduardo Cadena-Cruz, and Christian D. Alcívar-León. "Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis." Molecules 27, no. 19 (October 9, 2022): 6708. http://dx.doi.org/10.3390/molecules27196708.

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Анотація:

Many heterocyclic compounds can be synthetized using diaza-1,3-butadienes (DADs) as key structural precursors. Isolated and in situ diaza-1,3-butadienes, produced from their respective precursors (typically imines and hydrazones) under a variety of conditions, can both react with a wide range of substrates in many kinds of reactions. Most of these reactions discussed here include nucleophilic additions, Michael-type reactions, cycloadditions, Diels–Alder, inverse electron demand Diels–Alder, and aza-Diels–Alder reactions. This review focuses on the reports during the last 10 years employing 1,2-diaza-, 1,3-diaza-, 2,3-diaza-, and 1,4-diaza-1,3-butadienes as intermediates to synthesize heterocycles such as indole, pyrazole, 1,2,3-triazole, imidazoline, pyrimidinone, pyrazoline, -lactam, and imidazolidine, among others. Fused heterocycles, such as quinazoline, isoquinoline, and dihydroquinoxaline derivatives, are also included in the review.

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16

Lystsova, Ekaterina A., Ekaterina E. Khramtsova, and Andrey N. Maslivets. "Acyl(imidoyl)ketenes: Reactive Bidentate Oxa/Aza-Dienes for Organic Synthesis." Symmetry 13, no. 8 (August 17, 2021): 1509. http://dx.doi.org/10.3390/sym13081509.

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Polyfunctional building blocks are essential for the implementation of diversity-oriented synthetic strategies, highly demanded in small molecule libraries’ design for modern drug discovery. Acyl(imidoyl)ketenes are highly reactive organic compounds, bearing both oxa- and aza-diene moieties, conjugated symmetrically to the ketene fragment, enabling synthesis of various skeletally diverse heterocycles on their basis. The highlights of reactions utilizing acyl(imidoyl)ketenes are high yields, short reaction time (about several minutes), high selectivity, atom economy, and simple purification procedures, which benefits the drug discovery. The present review focuses on the approaches to thermal generation of acyl(imidoyl)ketenes, patterns of their immediate transformations via intra- and intermolecular reactions, including the reactions of cyclodimerization, in which either symmetric or dissymmetric heterocycles can be formed. Recent advances in investigations on mechanisms, identifications of intermediates, and chemo- and regioselectivity of reactions with participation of acyl(imidoyl)ketenes are also covered.

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17

Vodnala, Sumathi, Anagani Kanaka Durga Bhavani, Shankaraiah Pagilla, Muralidhar Allam, Nagamani Rayala, Anwita Mudiraj, and Phanithi Prakash Babu. "Synthesis and Cytotoxic Studies of Quinazoline-Triazole Hybrid Aza Heterocycles." Russian Journal of General Chemistry 91, no. 11 (November 2021): 2304–10. http://dx.doi.org/10.1134/s1070363221110189.

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18

Kitamura, Mitsuru, and Koichi Narasaka. "Synthesis of Aza-Heterocycles from Oximes by Amino-Heck Reaction." Chemical Record 2, no. 4 (July 2002): 268–77. http://dx.doi.org/10.1002/tcr.10030.

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19

Ma, Shengming. "Heterocycles based on the chemistry of alkylidenecyclopropanes and (aza)-cyclopropenes." Pure and Applied Chemistry 80, no. 4 (January 1, 2008): 695–706. http://dx.doi.org/10.1351/pac200880040695.

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Анотація:

Alkylidenecyclopropyl, cyclopropenyl, or azacyclocyclopropenyl ketones or carboxylates have been demonstrated to be versatile starting materials for the synthesis of oxygen- and/or nitrogen-containing heterocycles. The reactivities and regioselectivities may be nicely controlled by subtle choice of the catalysts and reaction condition parameters.

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20

Majumdar, K. C., and S. K. Samanta. "Studies in aza-Claisen rearrangement: synthesis of dimedone-annelated unusual heterocycles." Tetrahedron 57, no. 23 (June 2001): 4955–58. http://dx.doi.org/10.1016/s0040-4020(01)00405-7.

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21

Marini, Francesca, Martina Palomba, Luana Bagnoli, and Claudio Santi. "Synthesis of Pyrrolidinols by Radical Additions to Carbonyls Groups." Proceedings 41, no. 1 (November 14, 2019): 20. http://dx.doi.org/10.3390/ecsoc-23-06606.

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Анотація:

Radical cyclizations represent powerful synthetic strategies for the assembling of heterocycles. Most radical cyclizations are based on the addition to C C double or triple bonds. On the contrary, the addition to C O double bonds is rarely reported, since it proceeds reversibly due to the formation of thermodynamically unfavorable alkoxy radicals. Herein we report our attempts to construct substituted pyrrolidin-3-ols by tin-mediated radical cyclization of 5-phenylseleno-3-aza-pentanals. These rings are widely represented in natural products and drug candidates with various biological activities.

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22

Rulev, Alexander Yu, Alexey R. Romanov, Alexander V. Popov, Evgeniy V. Kondrashov, and Sergey V. Zinchenko. "Reaction of Bromoenones with Amidines: A Simple Catalyst-Free Approach to Trifluoromethylated Pyrimidines." Synthesis 52, no. 10 (March 9, 2020): 1512–22. http://dx.doi.org/10.1055/s-0040-1707969.

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A facile one-pot synthesis of trifluoromethylated pyrimidines has been achieved by the treatment of fluorinated 2-bromoenones with aryl- and alkylamidines. The assembly of pyrimidine core proceeds by the cascade reactions via aza-Michael addition–intramolecular cyclization–dehydrohalogenation/dehydration sequence. This strategy is featured by high selectivity and mild reaction conditions giving the target heterocycles in high yields (up to 99%). The unique influence of trifluoromethyl group on the reaction path is demonstrated.

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23

Pinho e Melo, Teresa M. V. D. "Chemistry of aza- and diazafulvenium methides in heterocyclic synthesis." Pure and Applied Chemistry 88, no. 5 (May 1, 2016): 457–75. http://dx.doi.org/10.1515/pac-2016-0404.

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AbstractAza- and diazafulvenium methide systems are versatile building blocks for the synthesis of pyrroles and pyrazoles. These extended dipoles participate in sigmatropic [1,8]H shifts and 1,7-electrocyclizations giving vinyl pyrroles and pyrazoles. Under flash vacuum pyrolysis conditions these heterocycles undergo interesting rearrangements. Aza- and diazafulvenium methides can be intercepted by dipolarophiles. Derivatives with carboxylate groups at C-4 and/or C-5 act exclusively as 1,7-dipoles affording products resulting from the addition across the 1,7-positions. These 1,7-cycloadducts include chlorin and bacteriochlorin type macrocycles as well as steroidal analogues, compounds with relevance in medicinal chemistry. In contrast with this chemical behavior, 5-trifluoromethylazafulvenium methides can participate in both 1,7- and 1,3-dipolar cycloadditions. The generation and reactivity of benzodiazafulvenium methides is also discussed.

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24

Cherkasov, V. M., and N. A. Kapran. "Aza-1,3-butadienes in synthesis of nitrogen-containing six-membered heterocycles (review)." Chemistry of Heterocyclic Compounds 28, no. 10 (October 1992): 1101–8. http://dx.doi.org/10.1007/bf00529568.

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25

Llona-Minguez, Sabin, Matthieu Desroses, Artin Ghassemian, Sylvain A. Jacques, Lars Eriksson, Rebecka Isacksson, Tobias Koolmeister, Pål Stenmark, Martin Scobie, and Thomas Helleday. "Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza-Heterocycles." Chemistry - A European Journal 21, no. 20 (March 25, 2015): 7394–98. http://dx.doi.org/10.1002/chem.201406549.

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26

Geng, Zhi-Cong, Jian Chen, Ning Li, Xiao-Fei Huang, Yong Zhang, Ya-Wen Zhang та Xing-Wang Wang. "Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives". Beilstein Journal of Organic Chemistry 8 (9 жовтня 2012): 1710–20. http://dx.doi.org/10.3762/bjoc.8.195.

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The catalytic synthesis of nitrogen-containing heterocycles is of great importance to medicinal and synthetic chemists, and also a challenge for modern chemical methodology. In this paper, we report the synthesis of pyrazolidine derivatives through a domino aza-Michael/hemiacetal sequence with chiral or achiral secondary amines as organocatalysts. Thus, a series of achiral pyrazolidine derivatives were obtained with good yields (up to 90%) and high diastereoselectivities (>20:1) with pyrrolidine as an organocatalyst, and enantioenriched pyrazolidines are also achieved with good results (up to 86% yield, >10/1 regioselectivity, >20:1 dr, 99% ee) in the presence of (S)-diphenylprolinol trimethylsilyl ether catalyst.

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27

Fustero, Santos, María Sánchez-Roselló, and Carlos del Pozo. "Asymmetric tandem reactions: New synthetic strategies." Pure and Applied Chemistry 82, no. 3 (February 18, 2010): 669–77. http://dx.doi.org/10.1351/pac-con-09-09-07.

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Анотація:

The use of domino and multicomponent reactions in asymmetric synthesis is constantly increasing nowadays. This allows for the synthesis of complex molecules in a single synthetic sequence, usually with high atom economy. Herein, we report three examples of new asymmetric tandem reactions recently developed in our laboratories, giving rise to new families of enantiomerically enriched fluorinated and nonfluorinated heterocycles. Thus, 1,4-dihydropyridines (1,4-DHPs) bearing fluorinated substituents at C6 were assembled by means of a Hantzsch-type reaction; cyclic β-amino carbonyl derivatives were prepared using a cross-metathesis (CM)–intramolecular aza-Michael sequence; while fluorinated indolines were obtained, for the first time, in a tandem nucleophilic addition–intramolecular aromatic substitution.

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28

Vinogradov, Maxim G., Olga V. Turova, and Sergei G. Zlotin. "Recent advances in the asymmetric synthesis of pharmacology-relevant nitrogen heterocycles via stereoselective aza-Michael reactions." Organic & Biomolecular Chemistry 17, no. 15 (2019): 3670–708. http://dx.doi.org/10.1039/c8ob03034k.

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Анотація:

In this review, recent applications of a stereoselective aza-Michael reaction for asymmetric synthesis of naturally occurring N-containing heterocyclic scaffolds and their usefulness to pharmacology are summarized.

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29

El Bouakher, Abderrahman, Arnaud Martel та Sébastien Comesse. "α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles". Organic & Biomolecular Chemistry 17, № 37 (2019): 8467–85. http://dx.doi.org/10.1039/c9ob01683j.

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30

Singh, Surjeet, Ranjay Shaw, Shally, Sandeep Chaudhary, Abhinav Kumar, and Ramendra Pratap. "Synthesis of arylated and aminated naphthalenes and their synthetic applications for aza-heterocycles." Tetrahedron 72, no. 41 (October 2016): 6436–43. http://dx.doi.org/10.1016/j.tet.2016.08.044.

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31

Timmer, Mattie S. M., Martijn D. P. Risseeuw, Martijn Verdoes, Dmitri V. Filippov, Jasper R. Plaisier, Gijsbert A. van der Marel, Herman S. Overkleeft, and Jacques H. van Boom. "Synthesis of functionalized heterocycles via a tandem Staudinger/aza-Wittig/Ugi multicomponent reaction." Tetrahedron: Asymmetry 16, no. 1 (January 2005): 177–85. http://dx.doi.org/10.1016/j.tetasy.2004.11.079.

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32

Burgin, Ryan N., Simon Jones, and B. Tarbit. "Scope and limitations of the Minisci reaction for the synthesis of aza-heterocycles." Tetrahedron Letters 50, no. 49 (December 2009): 6772–74. http://dx.doi.org/10.1016/j.tetlet.2009.09.112.

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33

Whelligan, Daniel K., Douglas W. Thomson, Dawn Taylor, and Swen Hoelder. "Two-Step Synthesis of Aza- and Diazaindoles from Chloroamino-N-heterocycles Using Ethoxyvinylborolane." Journal of Organic Chemistry 75, no. 1 (January 2010): 11–15. http://dx.doi.org/10.1021/jo902143f.

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34

Lugiņina, Jevgeņija, and Māris Turks. "Non-activated aziridines as building blocks for the synthesis of aza-heterocycles (microreview)." Chemistry of Heterocyclic Compounds 52, no. 10 (October 2016): 773–75. http://dx.doi.org/10.1007/s10593-016-1962-z.

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35

El-Ebiary, N. M., R. H. Swellem, and G. A. M. Nawwar. "Design, Synthesis and Anticancer Activity of Aza Heterocycles Containing Gallate Moiety (Part III)." Pharmaceutical Chemistry Journal 51, no. 1 (April 2017): 39–48. http://dx.doi.org/10.1007/s11094-017-1554-y.

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36

Majumdar, K. C., and S. K. Samanta. "ChemInform Abstract: Studies in Aza-Claisen Rearrangement: Synthesis of Dimedone-Anellated Unusual Heterocycles." ChemInform 32, no. 37 (May 24, 2010): no. http://dx.doi.org/10.1002/chin.200137055.

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37

Albenque-Rubio, Sandra, Jean Guillon, Anita Cohen, Patrice Agnamey, Solène Savrimoutou, Stéphane Moreau, Jean-Louis Mergny, et al. "Synthesis and Antimalarial Evaluation of New 1,3,5-tris[(4-(Substituted-aminomethyl)phenyl)methyl]benzene Derivatives: A Novel Alternative Antiparasitic Scaffold." Drugs and Drug Candidates 2, no. 3 (August 8, 2023): 653–72. http://dx.doi.org/10.3390/ddc2030033.

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Анотація:

A series of new 1,3,5-tris[(4-(substituted-aminomethyl)phenyl)methyl]benzene compounds were designed, synthesized, and evaluated in vitro against two parasites (Plasmodium falciparum and Leishmania donovani). The biological results showed antimalarial activity with IC50 values in the sub and μM range. The in vitro cytotoxicity of these new aza polyaromatic derivatives was also evaluated on human HepG2 cells. The 1,3,5-tris[(4-(substituted-aminomethyl)phenyl)methyl]benzene 1m was found as one of the most potent and promising antimalarial candidates with a ratio of cytotoxic to antiprotozoal activities of 83.67 against the P. falciparum CQ-sensitive strain 3D7. In addition, derivative 1r was also identified as the most interesting antimalarial compound with a selectivity index (SI) of 17.28 on the W2 P. falciparum CQ-resistant strain. It was previously described that the telomeres of P. falciparum could be considered as potential targets of these kinds of aza heterocycles; thus, the ability of these new derivatives to stabilize the parasitic telomeric G-quadruplexes was measured through a FRET melting assay.

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38

Adda, Abdelghani, and Hayat Sediki. "Theoretical Study of the Aza˗Wittig Reaction, Me3P=NR (R = Methyl or Phenyl) with Aldehyde Using the DFT and DFT-D Methods (Dispersion Correction)." Chemistry Proceedings 3, no. 1 (November 14, 2020): 47. http://dx.doi.org/10.3390/ecsoc-24-08349.

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: The Aza-Wittig reaction plays an important role in organic transformations and has seen considerable development in the construction of cyclic and acyclic compounds in neutral solvents in the absence of catalysts with a high yield of products. Today, the use of iminophosphoranes (phosphazenes) has become a powerful tool in organic synthesis strategies directed toward the construction of nitrogenous heterocycles. These can react with carbonyl compounds, an excellent method for the construction of C=N double bonds via intermolecular and intramolecular Aza-Wittig reactions. In this study, we are interested in the theoretical study of the reaction path of the Aza˗Wittig reaction between trimethyl-iminophosphoranes (CH3)3P=NR, R = CH3 or Ph) for the two-substituent methyl and phenyl with acetaldehyde, including continuum solvation. Our calculations were carried out by means of ab initio calculations using DFT (Density Function Theory) with a dispersion correction term using the Grimme method in the program Gaussian09, using the functional B3LYP-GD3BJ with a 6-31G** base. The results obtained allowed us to highlight the mechanisms of the Aza-Wittig reaction in particular after the addition of the term of dispersion correction or van der Waals correction, which provides a new description of this reaction and its chemical path.

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39

Renslo, Adam R., Hongwu Gao, Priyadarshini Jaishankar, Revathy Venkatachalam, and Mikhail F. Gordeev. "Synthesis of Aza-, Oxa-, and Thiabicyclo[3.1.0]hexane Heterocycles from a Common Synthetic Intermediate." Organic Letters 7, no. 13 (June 2005): 2627–30. http://dx.doi.org/10.1021/ol050730h.

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40

Olier, Clarisse, Mustapha Kaafarani, Stéphane Gastaldi, and Michèle P. Bertrand. "Synthesis of tetrahydropyrans and related heterocycles via prins cyclization; extension to aza-prins cyclization." Tetrahedron 66, no. 2 (January 2010): 413–45. http://dx.doi.org/10.1016/j.tet.2009.10.069.

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41

CHERKASOV, V. M., and N. A. KAPRAN. "ChemInform Abstract: Aza-1,3-butadienes in the Synthesis of Nitrogen-Containing 6-Membered Heterocycles." ChemInform 24, no. 44 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199344323.

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42

Llona-Minguez, Sabin, Matthieu Desroses, Artin Ghassemian, Sylvain A. Jacques, Lars Eriksson, Rebecka Isacksson, Tobias Koolmeister, Paal Stenmark, Martin Scobie, and Thomas Helleday. "ChemInform Abstract: Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza-Heterocycles." ChemInform 46, no. 40 (September 17, 2015): no. http://dx.doi.org/10.1002/chin.201540135.

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43

Prishchenko, Andrey A., Roman S. Alekseyev, Mikhail V. Livantsov, Olga P. Novikova, Ludmila I. Livantsova, Vladimir I. Terenin, and Valery S. Petrosyan. "Synthesis of new functionalized mono- and diphosphonic acids with five-membered aza-heterocycles moieties." Heteroatom Chemistry 28, no. 1 (December 13, 2016): e21353. http://dx.doi.org/10.1002/hc.21353.

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44

Race, Nicholas J., Ian R. Hazelden, Adele Faulkner, and John F. Bower. "Recent developments in the use of aza-Heck cyclizations for the synthesis of chiral N-heterocycles." Chemical Science 8, no. 8 (2017): 5248–60. http://dx.doi.org/10.1039/c7sc01480e.

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45

Rostovskii, Nikolai V., Mikhail S. Novikov, and Alexander F. Khlebnikov. "Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes." Organics 2, no. 3 (September 14, 2021): 313–36. http://dx.doi.org/10.3390/org2030017.

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Conjugated azapolyenes (azabuta-1,3-dienes, aza-/diaza-/oxaza-/oxadiazahexa-1,3,5-trienes) are highly reactive in electrocyclization reactions, which makes them convenient precursors for the synthesis of a wide range of four-, five-, and six-membered nitrogen heterocycles that are of relevance for medicinal chemistry. Ring opening reactions of 2H-azirines and azoles containing an N–N or N–O bond, initiated by a transition metal carbene, have become increasingly important in recent years, since they easily allow the generation of azapolyenes with different numbers of double bonds and heteroatoms in various positions. This review summarizes the literature, published mainly in the last decade, on the synthetic and mechanistic aspects of electrocyclizations of azapolyenes generated by the carbene method.

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46

Narasaka, K. "Synthesis of azaheterocycles from oxime derivatives." Pure and Applied Chemistry 75, no. 1 (January 1, 2003): 19–28. http://dx.doi.org/10.1351/pac200375010019.

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Electrophilic amination of Grignard reagents has been accomplished by using O-sulfonyloximes as amination reagents. Benzophenone O-sulfonyloxime derivatives react with Grignard reagents on sp2 nitrogen, yielding primary amines by successive hydrolysis of the resulting N-alkylimines. Various cyclic imines are synthesized by Pd-catalyzed reaction from olefinic oxime derivatives. That is, treatment of O-pentafluorobenzoyloximes of olefinic ketones with a catalytic amount of Pd(PPh3)4 and triethylamine affords nitrogen-containing heterocycles, such as pyrroles, pyridines, isoquinolines, spiro-imines, and aza-azulenes. This reaction proceeds via the initial formation of alkylideneaminopalladium(II) species generated by oxidative addition of the oximes to the Pd(0) complex, and the following intramolecular amination on the olefinic moiety. Cyclic imines are prepared from γ,δ-unsaturated O-acetyloximes by treatment with acetic acid and 1,4-cyclohexadiene in the presence of a catalytic amount of 1,5-naphthalene-diol. γ,δ-Unsaturated ketone O-methoxycarbonyloximes are transformed to 2-bromomethyl-3,4 dihydro-2H-pyrroles by the action of a catalytic amount of Cu(I) bromide dimethyl sulfide complex and lithium bromide.

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47

Magoo, D., Komal Aggarwal, Shruti Gupta, and Kalawati Meena. "Enamines and their variants as intermediates for synthesis of aza-heterocycles with applications in MCRs." Tetrahedron 103 (January 2022): 132545. http://dx.doi.org/10.1016/j.tet.2021.132545.

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48

Takizawa, Shinobu. "Organocatalytic Synthesis of Highly Functionalized Heterocycles by Enantioselective aza-Morita–Baylis–Hillman-Type Domino Reactions." Chemical and Pharmaceutical Bulletin 68, no. 4 (April 1, 2020): 299–315. http://dx.doi.org/10.1248/cpb.c19-00900.

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49

Wu, Jiajun, and Christophe Darcel. "Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles." Journal of Organic Chemistry 86, no. 1 (December 16, 2020): 1023–36. http://dx.doi.org/10.1021/acs.joc.0c02505.

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50

Eguchi, Shoji, Takashi Okano, and Tomohiro Okawa. "ChemInform Abstract: Synthesis of Heterocyclic Natural Products and Related Heterocycles by the Aza-Wittig Methodology." ChemInform 30, no. 27 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199927287.

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