Synthesis and transformations of trifluoromethyl-substituted cyanopyrrolines

被引：1

作者：

Volkonskii, A. Yu. ^{[1
]}

Kagramanov, N. D. ^{[1
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Build 1,28 Ul Vavilova, Moscow 119334, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2023年 / 72卷 / 07期

关键词：

trifluoromethyl-substituted cyanopyrrolines and -pyrrolidines; (fluoroalkyl)-cyanoprop-2-enylidene-substituted 1; 3-diazetidines; base catalysis; aerobic oxidation; 1; 3-dipolar cycloaddition; CYCLOADDITION;

D O I：

10.1007/s11172-023-3934-7

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

3-Cyano-1-methyl-4-trifluoromethyl-3-pyrroline, as well as 4-cyano-1-methyl-3-trifluoromethyl- and 3-cyano-1-methyl-4-trifluoromethyl-2-pyrrolines were synthesized under DBU catalysis by heating of Z-3-cyano-4-ethoxy-1-methyl-4-trifluoromethyl-pyrrolidine in vacuo. 3-Cyano-1-methyl-4-trifluoromethyl-3-pyrroline undergoes redox disproportionation catalyzed by potassium tert-butoxide to form 2,4-bis(2-cyano-1-trifluoromethylprop-2-enylidene)-1,3-dimethyl-1,3-diazetidine and E-/Z-isomers of 3-cyano-1-methyl-4-trifluoromethylpyrrolidine. The same 1,3-diazetidine is formed by oxidation of 3-cyano-1-methyl-4-trifluoromethyl-3-pyrroline with atmospheric oxygen. Individual E- and Z-isomers of 3-cyano-1-methyl-4-trifluoromethylpyrrolidine were obtained by stereospecific 1,3-dipolar cycloaddition of E- and Z-isomers of 4,4,4-trifluorobut-2-enonitrile to N-methyl(methaniminio)-N-methylide generated in situ.

引用

页码：1560 / 1568

页数：9

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