88609-14-7Relevant articles and documents
Heteropentalenes. The Thermal Addition of 1,3-Dimethylpyrazolobenzotriazole to Dimethyl Acetylenedicarboxylate
Albini, Angelo,Bettinetti, Gianfranco,Minoli, Giovanna
, p. 2491 - 2494 (2007/10/02)
The title compound (3) reacts with dimethyl acetylenedicarboxylate with addition onto the azomethinimine moiety to give dimethyl 2a,4-dimethyl-4a,8b,8c-triazapentalenoindene-1,2-dicarboxylate (7) via a zwitterionic intermediate which can be trapped by protic solvents, e.g. methanol or water to give dimethyl 2--3-methoxymaleate (8) or tetramethyl 3,3'-bis-2,2'-oxydimaleate (9), respectively.The cycloadduct (7) undergoes spontaneous retrocycloaddition to dimethyl 3-methylpyrazolobenzo triazole-1,2-dicarboxylate (12) and radical cleavage to yield, unexpectedly, methyl 4,5-dihydro-2-methyl-4-oxopyrazoloquinoxaline-3-carboxylate (17) as the main product together with small amounts of two benzotriazolylpentenones (14) and (15).