Abstract
The reactions of 3-acylindoles [3-indolecarbaldehyde (1), 3-acetylindole (12), 3-benzoylindole (13), and N-substituted 3-indolecarbaldehydes (20a-d)] with diethyl phosphorocyanidate (DEPC) in the presence of lithium cyanide (LiCN) are described. Treatment of 1 with DEPC and LiCN gave a mixture of (E)- and (Z)-3-cyanomethylene-1-diethylphosphono-2-hydroxyindolines (2 and 3). On the other hand, reaction of 12, 13 and 20a-d with DEPC and LiCN afforded 2-cyano-3-indoleacetonitrile derivatives (16, 19 and 21a-d). Strong base-induced cycloaddition reactions of 2-cyano-1-methyl-3-indoleacetonitrile (21a) with carbon-carbon triple bonds were carried out and gave the corresponding condensation products, 1-amino-4-cyanocarbazoles (22a-e), 6-amino-11-cyanobenzo[b]carbazole (23), pyrido[4, 3-b]carbazole (25), and pyrido[3, 4-b]carbazole (26), in moderate yields.
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