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Nitriles in heterocyclic synthesis: The reaction of ethyl 2-oxoindoliden-3-ylidene cyanoacetate and of 3-dicyanoethylideneindoliden-2-one with phenols and amines

✍ Scribed by Kamal Usef Sadek; Maghraby Ali Selim; Mohamed Ali; Mohamed Hilmy Elnagdi

Book ID: 102229834
Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 320 KB
Volume: 6
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520060618

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✦ Synopsis

The reactions of ethyl 2-oxoindoliden-3-ylidene cyanoacetate (2a) and of 3-dicyanoethylideneindoliden-2-one (2b) with phenols and amines have been reported. 0 1996 John Wiley & Sons, Inc. a$-Unsaturated nitriles are highly reactive reagents and have been extensively utilized in heterocyclic synthesis [ 11. Reactions of nucleophiles with these reagents normally take place at the @-carbon . Moreover, when C-@ carries other electron-attracting functional groups, reactions at the a carbon also occur . Thus, whereas ethyl 2-oxoindoliden-3-ylidene cyanoacetate (2a) and 3-dicyanoethylideneindoliden-2-one (2b) have been reported to react with pyrazolones and with active methylene ketones to yield spiropyranopyrazoles, phenols and amines have recently been reported to react with 4-(dicyanomethylene)-3-methyl-1 -phenyl-2-pyrazolin-~~

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