T. Kurihara, K. Nasu, Y. Adachi
Sep 6, 1983
Citations
0
Influential Citations
13
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
The reactions of 3-acetyl-4-ethoxycarbonyl- or 3,4-diethoxycarbonylpyrrolo[1,2-a]pyrimidine derivatives 7a,b, which were prepared by condensation of the 2-aminopyrrole (4) with ethyl 3-ethoxymethylene-2,4-dioxovalerate (5a) or ethyl ethoxymethyleneoxaloacetate (5b), with diazomethane are described. Thus, reaction of 7a, with diazomethane gave ethyl 2a-acetyl-7-cyano-2a,3a-dihydro-5,6-dimethyl-3H -cyclopropa[e]pyrrolo[1,2-a]pyrimidine-3a-carboxylate (11) in 74% yield, which was readily transformed into the 1-pyrrol-2-yl-pyrrole (18) by treatment with potassium hydroxide. On the other hand, reaction of 7b with diazomethane afforded three products whose structures were assigned as diethyl 7-cyano-2a,3a-dihydro-5,6-dimethyl-3H-cyclopropa[e]pyrrolo[1,2-a]pyrimidine-2a,3a-carboxylate (20), 6-cyano-7,8-dimethyl-3a,3b,5,9a-tetrahydro-4H -aziridino[c]-1H or 3H-pyrazolo[3,4-e]pyrrolo[1,2-a]pyrimidine-3a,9a-dicarboxylates (21,22). Ring Transformation of 20 to 25 was not observed.