jo980082y_si_001.pdf (436.8 kB)
2-Benzotriazolylaziridines and Their Reactions with Diethyl Acetylenedicarboxylate
journal contribution
posted on 1998-12-31, 00:00 authored by Alan R. Katritzky, Jiangchao Yao, Weiliang Bao, Ming Qi, Peter J. Steel1-Alkyl-2-benzotriazolylaziridines (3a,b and 8a−g) are synthesized by two routes utilizing a novel
benzotriazolyl-substituted carbenoid or 1,2-dibromoethylbenzotriazole. Lithiation of 3b and 8e at
the position a to benzotriazole and subsequent trapping with alkyl halides leads to the 1,2-dialkyl-2-benzotriazolylaziridine analogues 12 and 20. Compounds 3a and 3b react with acetylenedicarboxylic ester by C−C bond breaking to give pyrrole-3,4-dicarboxylic esters (14a,b). By contrast,
compounds 8a−d and 20 react with acetylenedicarboxylic ester by C−N bond breaking and form
pyrrole-2,3-dicarboxylic esters 18a−d and 21. Structures of each type of pyrroledicarboxylic ester
are established by X-ray analysis.