Application of Vinyl Azides in Chemical Synthesis: A Recent Update

被引:127
作者
Hayashi, Hirohito [1 ]
Kaga, Atsushi [1 ]
Chiba, Shunsuke [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
DONOR-ACCEPTOR CYCLOPROPANES; CLICK-CHEMISTRY; RADICAL REACTIONS; MEDICINAL CHEMISTRY; CATALYZED SYNTHESIS; DIVERGENT SYNTHESIS; CONJUGATE ADDITION; AMIDE SYNTHESIS; CYCLOADDITION; CYCLIZATION;
D O I
10.1021/acs.joc.7b02455
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Among organic azides, vinyl azides have shown versatile chemical reactivities in the recent development of new synthetic methodologies mainly for nitrogen-containing molecules. This synopsis highlights and discusses recent advances on use of vinyl azides in chemical synthesis as a radical acceptor and an enamine-type nucleophile.
引用
收藏
页码:11981 / 11989
页数:9
相关论文
共 96 条
[1]   Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].
Agalave, Sandip G. ;
Maujan, Suleman R. ;
Pore, Vandana S. .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718
[2]   Site-Specific Dual Functionalization of Cysteine Residue in Peptides and Proteins with 2-Azidoacrylates [J].
Ariyasu, Shinya ;
Hayashi, Hirohito ;
Xing, Bengang ;
Chiba, Shunsuke .
BIOCONJUGATE CHEMISTRY, 2017, 28 (04) :897-902
[3]   THEORETICAL-STUDY OF THE BARRIER TO NITROGEN INVERSION IN N-CYANOFORMIMINE AND N-DIAZOFORMIMINE - MECHANISM OF THE SCHMIDT REACTION [J].
BACH, RD ;
WOLBER, GJ .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (02) :239-245
[4]   MECHANISM OF THE REACTION OF TRIALKYLBORANES WITH ALPHA-AZIDOSTYRENE [J].
BAMFORD, AF ;
COOK, MD ;
ROBERTS, BP .
TETRAHEDRON LETTERS, 1983, 24 (35) :3779-3782
[5]   Click Chemistry and Bioorthogonal Reactions: Unprecedented Selectivity in the Labeling of Biological Molecules [J].
Best, Michael D. .
BIOCHEMISTRY, 2009, 48 (28) :6571-6584
[6]   Natural Products and Their Biological Targets: Proteomic and Metabolomic Labeling Strategies [J].
Boettcher, Thomas ;
Pitscheider, Maximilian ;
Sieber, Stephan A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (15) :2680-2698
[7]   FORMAL SYNTHESIS OF THE ANTITUMOUR ANTIBIOTIC CC-1065 [J].
BOLTON, RE ;
MOODY, CJ ;
PASS, M ;
REES, CW ;
TOJO, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2491-2499
[8]   Iron(II) Triflate as a Catalyst for the Synthesis of Indoles by Intramolecular C-H Amination [J].
Bonnamour, Julien ;
Bolm, Carsten .
ORGANIC LETTERS, 2011, 13 (08) :2012-2014
[9]   Organic azides:: An exploding diversity of a unique class of compounds [J].
Bräse, S ;
Gil, C ;
Knepper, K ;
Zimmermann, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240
[10]  
Brase S., 2010, Organic Azides, Syntheses and Applications