219924-84-2Relevant academic research and scientific papers
2-Benzotriazolylaziridines and their reactions with diethyl acetylenedicarboxylate
Katritzky, Alan R.,Yao, Jiangchao,Bao, Weiliang,Qi, Ming,Steel, Peter J.
, p. 346 - 350 (2007/10/03)
1-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.
