89374-74-3Relevant academic research and scientific papers
Diels-Alder Reaction of 2-indoles with Acrylonitrile, Ethyl acrylate and Acrolein Acetal
Narasimhan, N. S.,Kusurkar, R. S.
, p. 846 - 849 (2007/10/02)
Diels-Alder reaction of N-methyl-2-(2-methoxyvinyl) indole (1) with acrylonitrile gives the cycloaddition compound 3, which is dehydrogenated by DDQ in benzene to the carbazole (4).The reaction of 1 with ethyl and methyl acrylates also gives cycloaddition compounds which, however, are dehydrogenated by DDQ, to carbazoles (6) and (8) in benzene with loss of the methoxy group, and to 9 in ethanol solution where an ethoxy group has been introduced at 4-position.Diels-Alder reaction of N-methyl-2-(2-nitrovinyl) indole (2) with acrylonitrile, methyl acrylate and acrolein acetal gives the carbazoles (11, 12, 13, 14) directly by the loss of nitro group and aromatisation.A "dimeric" compound (10) is also obtained in the latter reactions.
