109662-81-9Relevant articles and documents
Synthesis and Cycloaddition Reaction of 2-Cyano-3-indoleacetonitriles
Kurihara, Takushi,Hanakawa, Mitsuko,Harusawa, Shinya,Yoneda, Ryuji
, p. 4545 - 4553 (2007/10/02)
The reactions of 3-acylindoles 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-cyanobenzocarbazole (23), pyridocarbazole (25), and pyridocarbazole (26), in moderate yields.Keywords-diethyl phosphorocyanidate; cyanophosphorylation; 3-cyanomethyleneindoline; 2-cyano-3-indoleacetonitrile; orthoquinodimethane; acetylenic dienophile; 1-amino-4-cyano-carbazole; benzocarbazole; pyridocarbazole; pyridocarbazole