Synthesis of 2-alkoxycarbonyl enamino thioaldehydes and selenaldehydes (as pentacarbonyltungsten(0) complexes). Improved synthesis of simple and 2-cyano enamino thioaldehydes and some chemical reactions of these compounds
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1241-1252
- https://doi.org/10.1039/p19890001241
Abstract
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(0) 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.This publication has 1 reference indexed in Scilit:
- THE TOTAL SYNTHESIS OF CHLOROPHYLLJournal of the American Chemical Society, 1960