Journal of the Chemical Society. Perkin transactions I p. 1403 - 1407 (1996)
Update date:2022-08-24
Topics:
Murashima, Takashi
Fujita, Ken-Ichi
Ono, Kazuo
Ogawa, Takuji
Uno, Hidemitsu
Ono, Noboru
Nitro heteroarenes react with ethyl isocyanoacetate in the presence of 1,8-diazabicyclo[5.4.0]undecene (DBU) to give pyrroles or pyrimidine N-oxide depending on the structure of the starting nitro compounds. For example, 4-nitro-2,1,3-benzothiadiazole 3a reacted with ethyl isocyanoacetate to give ethyl 2,1,3-benzothiadiazolo[3,4-c]pyrrole-2-carboxylate 4a (33%), while a similar reaction with 5-nitro-2,1,3-benzothiadiazole 3b gave the corresponding compound 4b (21%) as a sole product. A plausible mechanism for these reactions is presented.
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