144564-32-9Relevant academic research and scientific papers
CYCLOADDITION REACTION OF 3-CYANOINDOLIZINES WITH DIMETHYL ACETYLENEDICARBOXYLATE - FORMATION OF CYCLAZINES AND 1:2 ADDUCTS
Uchida, Takane,Matsumoto, Kiyoshi
, p. 149 - 150 (1980)
3-Cyano- and 3-cyano-6,8-dimethylindolizines (1a) and (1b) react with dimethyl acetylenedicarboxylate in refluxing toluene in the presence of Pd-C to give the cyclazines (4a) and (4b), respectively, while 3-cyano-7-methyl- and 3-cyano-7-benzylindolizines (1c) and (1d) affording the 1:2 adducts (6c) and (6d) along with cyclazine (4d).
Cycloadditions of Indolizine-3-carbonitriles with Dimethyl Acetylenedicarboxylate: Formation of Cyclazines and 1:2 Adducts
Matsumoto, Kiyoshi,Uchida, Takane,Yoshida, Hiroshi,Toda, Mitsuo,Kakehi, Akikazu
, p. 2437 - 2442 (2007/10/02)
Reactions of indolizine-3-carbonitriles with dimethyl acetylenedicarboxylate (DMAD), in the presence of Pd-C, gave the corresponding 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.
