121670-79-9Relevant academic research and scientific papers
Reactions of 1H-1,2- and 1H-1,3-Diazepines with Dimethyl Acetylenedicarboxylate
Kurita, Jyoji,Kakusawa, Naoki,Tsuchiya, Takashi
, p. 1880 - 1881 (1987)
The title reactions yield the 3a,7a-dihydropyrrolopyridines (2) and 3a,7a-dihydroindazoles (9), respectively, probably via the diazonine intermediates (4) and (8) derived from the initially formed ? cycloadducts; the indazoles (9) further react with the reagent to give the dimethyl phthalates (6) and the pyrazoles (7) via the ? cycloadducts (10).
Studies on Diazepines. XXX. Addition Reactions of Monocyclic Diazepines with Dimethyl Acetylenedicarboxylate Involving Diazonine Intermediates
Kurita, Jyoji,Kakusawa, Naoki,Tsuchiya, Takashi
, p. 4706 - 4710 (2007/10/02)
The reaction of the 1H-1,3-diazepines (8a-c) with dimethyl acetylenedicarboxylate (DMAD) gave the 3a, 7a-dihydropyrrolopyridines (9), probably via the 1,5-diazonine intermediates 11 derived from the initially formed ? cycloadducts 10.Similarly, the 1H-1,2-diazepines (15a-c), upon treatment with DMAD, produced the 3a,7a-dihydroindazoles (20), presumably via the ? cycloadducts 18 and the 1,2-diazonines 19 successively, but the dihydroindazoles (20) further reacted with the reagent to give the dimethyl phthalates (16) and the pyrazoles (17) as the final products via the ? cycloadducts 21.These results are the first examples of the reaction of fully unsaturated seven-membered heterocyclic rings with acetylenes.Keywords--1H-1,3-diazepine; 1H-1,2-diazepine; dimethyl acetylenedicarboxylate; cycloaddition; diazonine intermediate; 3a,7a-dihydropyrrolopyridine; 3a,7a-dihydroindazole; dimethyl phthalate; pyrazole
