Issue 2, 1988
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Polarized ketene S,S- and S,N-acetals. Part 52. Lead tetra-acetate oxidation of 3-anilino-3-methylthio-2-arylacrylonitriles. A novel approach to substituted indoles

Jai Narain Vishwakarma,   Abraham Thomas,   Satyam Apparao,   Hiriyakkanavar Ila  and  Hiriyakkanavar Junjappa  

Abstract

Lead tetra-acetate oxidation of 3-anilino-3-methylthio-2-phenylacrylonitrile (4a) gave the iminoacetate (5a) and 3-cyano-2-methylthio-1-phenylindole (6a). The corresponding methoxy substituted 2-arylacrylonitriles (4b–d), however, yielded the symmetric dimeric products (7a–c) and the unstable iminoacetates (5a–d) respectively under similar conditions. The corresponding p-chloro derivative (4e) afforded the stable iminoacetate (5e), dimer (7d), and 6-chloroindole (6e) in low yields. The iminoacetates (5a–e) could be cyclized to the respective indoles (6a–e) in the presence of boron trifluoride–diethyl ether. The probable mechanistic pathways for the formation of various products are described.

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Article information

DOI
https://doi.org/10.1039/P19880000169
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 169-173

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Polarized ketene S,S- and S,N-acetals. Part 52. Lead tetra-acetate oxidation of 3-anilino-3-methylthio-2-arylacrylonitriles. A novel approach to substituted indoles

J. N. Vishwakarma, A. Thomas, S. Apparao, H. Ila and H. Junjappa, J. Chem. Soc., Perkin Trans. 1, 1988, 169 DOI: 10.1039/P19880000169

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