Literature DB >> 32474890

Vinylazides: versatile synthons and magical precursors for the construction of N-heterocycles.

Zahra Tashrifi1,2, Mohammad Mohammadi-Khanaposhtani3,2, Bagher Larijani1,2, Halleh Hamedifar3,2, Samira Ansari4,5, Mohammad Mahdavi6,7.   

Abstract

Nowadays, application of vinylazides as precursors is a key method for the construction of N-heterocycles in organic synthesis. These versatile three-atom synthons can be converted into intermediates such as 2H-azirines, iminyl radicals, iminyl metal complexes, iminyl inions and nitrilium ions that subsequently afford a wide range of polyfunctional cyclic nitrogen-containing compounds. In this review, the reactions of vinylazides leading to these products (in the last decade) are categorized based on the types of the resulting N-heterocyclic rings and a brief and concise description of the reaction mechanisms is presented.
© 2020. Springer Nature Switzerland AG.

Entities:  

Keywords:  2H-azirines; N-heterocycles; Synthon; Vinylazides

Mesh:

Substances:

Year:  2020        PMID: 32474890     DOI: 10.1007/s11030-020-10106-1

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  20 in total

1.  Catalyst-free preparation of 1,2,4,5-tetrasubstituted imidazoles from a novel unexpected domino reaction of 2-azido acrylates and nitrones.

Authors:  Bao Hu; Zhao Wang; Ning Ai; Jie Zheng; Xing-Hai Liu; Shang Shan; Zhongwen Wang
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

Review 2.  Practical methodologies for the synthesis of indoles.

Authors:  Guy R Humphrey; Jeffrey T Kuethe
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

3.  Domino approach for the synthesis of pyrrolo[1,2-alpha]pyrazine from vinyl azides.

Authors:  Wenteng Chen; Miao Hu; Jianwei Wu; Hongbin Zou; Yongping Yu
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

Review 4.  α-Substituted vinyl azides: an emerging functionalized alkene.

Authors:  Junkai Fu; Giuseppe Zanoni; Edward A Anderson; Xihe Bi
Journal:  Chem Soc Rev       Date:  2017-11-27       Impact factor: 54.564

5.  Application of Vinyl Azides in Chemical Synthesis: A Recent Update.

Authors:  Hirohito Hayashi; Atsushi Kaga; Shunsuke Chiba
Journal:  J Org Chem       Date:  2017-11-03       Impact factor: 4.354

Review 6.  Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis.

Authors:  Bao Hu; Stephen G DiMagno
Journal:  Org Biomol Chem       Date:  2015-04-07       Impact factor: 3.876

7.  Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles: a formal total synthesis of lukianol A.

Authors:  J H Liu; Q C Yang; T C Mak; H N Wong
Journal:  J Org Chem       Date:  2000-06-16       Impact factor: 4.354

8.  Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and 1,3-dicarbonyl compounds.

Authors:  Yi-Feng Wang; Kah Kah Toh; Shunsuke Chiba; Koichi Narasaka
Journal:  Org Lett       Date:  2008-10-09       Impact factor: 6.005

9.  Scalable, divergent synthesis of meroterpenoids via "borono-sclareolide".

Authors:  Darryl D Dixon; Jonathan W Lockner; Qianghui Zhou; Phil S Baran
Journal:  J Am Chem Soc       Date:  2012-05-14       Impact factor: 15.419

10.  Mn(III)-mediated reactions of cyclopropanols with vinyl azides: synthesis of pyridine and 2-azabicyclo[3.3.1]non-2-en-1-ol derivatives.

Authors:  Yi-Feng Wang; Shunsuke Chiba
Journal:  J Am Chem Soc       Date:  2009-09-09       Impact factor: 15.419

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