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Synthesis of 2-llkoxycarbonyl enamino thioaldehydes and selenaldehydes (as Pentacarbonyltungsten(0) Complexes). Improved synthesis of simple and 2-cyano enamino thioaldehydes and some chemical reactions of these compounds

DOI: 10.1039/P19890001241

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1241 - 1252 (1989)

Update date:2022-08-05

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Authors:

Muraoka, MotomuMuraoka, Motomu

Yamamoto, TatsuoYamamoto, Tatsuo

Enomoto, KazuoEnomoto, Kazuo

Takeshima, TatsuoTakeshima, Tatsuo

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Article abstract of DOI:10.1039/P19890001241

A series of stable 2-alkoxycarbonyl enamino thioaldehydes (2a-g) were synthesized by solvolysis of the Vilsmeier salts (1) with aqueous or methanolic sodium hydrogen sulphide. Three 2-alkoxycarbonyl enamino selenaldehydes were obtained as the pentacarbonyltungsten(o) complexes (7a-c). The 2-cyano and simple enamino thioaldehydes (3a-m) and (6a-j) (including some new homologues obtained by an improved synthetic method) are described. Some reactions of 2-cyano and 2-alkoxycarbonyl enamino thioaldehydes were examined e.g. oxidation with MCPBA to give the isothiazoles (8). The symmetrically tetrasubstituted pyridines (9) were produced by bimolecular cyclisation under acidic conditions: hydrolysis in acidic 95% aq. EtOH gave the enamino aldehydes (11) and aroylacetonitriles (12) together with (9). The imines (13) were formed in good yield on reaction with primary amines.

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