1,3-Dipolar cycloaddition of 3-alkylsulfanyl-2-arylazo-3-(tert-cycloalkylamino)acrylonitriles with N-methyl- and N-phenylmaleimides
摘要:
A series of 1,2-diaza-1,3-butadienes with terminal S,N-acetal function were obtained and reacted with N-methyl- and N-phenylmaleimides. As a result of the 1,3-dipolar cycloaddition, a range of new functionalized nonaromatic heterocyclic compounds including: octahydro-1H-pyrrolo[3,4-a]indolizine, octahydropyrrolo[3',4':3,4]pyrrolo[1,2-a]azepine, hexahydropyrrolo[3',41:3,4]pyrrolo[2,1-c][1,4]oxazine and -thiazine, were obtained with good yields in mild conditions. Experimental and theoretic results allowed establishment of a relationship between the structures of the tert-cycloallcylamine group and the activity of the azomethine ylides generated. (C) 2014 Elsevier Ltd. All rights reserved.
Synthesis and oxidative cyclization of 3-amino-2-arylazo-5-tert-cycloalkylaminothiophenes
作者:N. P. Belskaya、A. V. Koksharov、A. I. Eliseeva、Z. Fan、V. A. Bakulev
DOI:10.1007/s10593-011-0799-8
日期:2011.8
A series of 3-amino-4-arylazo-4,5-dihydrothiophenes has been synthesized by the reaction of aryl-hydrazonocyanothioacetamides (containing a tert-cycloalkylamino group) with alpha-halo ketones, 2-chloroacetonitrile, or 4-nitrobenzyl bromide. Their oxidation in the presence of metal acetates was investigated. It was shown that heating in pyridine with Cu(OAc)(2) leads to the formation of thieno[3,4-d]-1,2,3-triazoliumolates.