Advances in synthesis and chemistry of aziridines

被引:39
|
作者
Singh, Girija S. [1 ]
机构
[1] Univ Botswana, Dept Chem, Gaborone, Botswana
来源
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 129 | 2019年 / 129卷
关键词
Aziridines; Asymmetric aziridination; Organocatalysis; Metal-carbenoid; alpha-Diazocarbonyls; Nitrenes; Aza-Darzens reaction; Aziridine-ring-opening; Azetidines; Pyrroles; Imidazoles; Pyrazoles; Thiazolidines; 1,3-Oxazolidin-2-ones; Pyrazines; Benzoxazines; 1,4-Diazapanes; Benzodiazepines; Diazocanes; RING-OPENING CYCLIZATION; CATALYTIC ASYMMETRIC AZIRIDINATION; ONE-POT SYNTHESIS; ACTIVATED AZIRIDINES; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; TERMINAL AZIRIDINES; ENANTIOSELECTIVE SYNTHESIS; N-TOSYLAZIRIDINES; 3+2 CYCLOADDITION;
D O I
10.1016/bs.aihch.2018.12.003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aziridines (azacyclopropanes) constitute the well-known class of heterocyclic compounds. The studies on synthesis and reactivity of aziridines have drawn tremendous interest of organic chemists. The main feature of interest in the chemistry of this molecule is the ring-strain associated with it. The synthetic endeavors to aziridines, once considered as challenging, have made significant advancements. A number of methods have been developed for synthesizing aziridines in enantiopure forms. The chemistry of aziridines focuses on ring-opening. Different types of nucleophiles react with aziridines leading to the cleavage of either C-C bond or one of the two C-N bonds leading to the formation of 1,2-difunctionalized compounds of interest as building blocks in organic synthesis. The opening of an aziridine ring followed by cycloaddition has opened up avenues for entry into diverse types of 4- to 11-membered heterocyclic compounds. The regioselectivity of the ring-opening is governed by steric and electronic factors on the ring. This chapter focuses on advancements in synthesis of aziridines and studies on their reactivity.
引用
收藏
页码:245 / 335
页数:91
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