1072912-64-1Relevant articles and documents
N-heterocyclic carbene induced cycloaddition reactions of indazoles with acetylenes to form a new ring system
Schmidt, Andreas,Snovydovych, Bohdan,Hemmen, Sascha
, p. 4313 - 4319 (2008)
Thermal decarboxylation of the mesomeric betaine 1,2-dimethylindazolium-3- carboxylate resulted in the formation of the N-heterocyclic carbene indazol-3-ylidene which deprotonated a second molecule of the betaine to give an azomethine ylide. This 1,3-dipole underwent a cycloaddition/decarboxylation sequence on treatment with ethyl or methyl 3-phenylpropiolate to give the new ring system 3,5-dihydro-2H-pyrrolo[1,2-b]indazole. By contrast, dimethyl or diethyl but-2-ynedioate (DMAD, DEAD) as the activated triple bond yielded this ring system with an ester group at the 9b-position, which originates from the acetylene derivative. Model reactions were carried out to elucidate the mechanisms of these reactions, and some trapping products of the N-heterocyclic carbene have been characterized.