Journal of the Chemical Society. Perkin transactions I p. 2437 - 2442 (1992)
Update date:2022-09-26
Topics:
Matsumoto, Kiyoshi
Uchida, Takane
Yoshida, Hiroshi
Toda, Mitsuo
Kakehi, Akikazu
Reactions of indolizine-3-carbonitriles with dimethyl acetylenedicarboxylate (DMAD), in the presence of Pd-C, gave the corresponding <2.2.3>cyclazines in low to moderate yields, whereas, in the absence of Pd-C, the same reactions afforded 1:2 molar products.The X-ray analysis of one of the 1:2 adducts established that the structure was dimethyl 2-cyano-3-styrylpyrrole-1,4-dicarboxylate.A possible mechanism is presented.
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