Reactions with 5‐Substituted 2‐Thiazolidinone‐4‐thiones (isorhodanines). III

Abstract

Treatment of 5‐arylidene‐2‐thiazolidinone‐4‐thiones 1 with diazomethane in etherchloroform mixture effects N‐methylation beside S‐methylation to give the products 2 and 3 respectively. The S‐alkylated derivatives 2 and 4 are obtained exclusively by the treatment of 1 with ethereal diazomethane or with ethyl bromoacetate, respectively. The N‐piperidinomethyl and N‐morphilinomethyl derivatives 5 were obtained by the MANNICH reaction on 1. The reaction of 1 with acrylonitrile or ethylacrylate in pyridine medium at room temperature yields the products 6. Subjecting 5‐arylazo‐2‐thiazolidinone‐4‐thiones 7 to the action of ethereal diazomethan gives both the S‐ and N‐methylated derivatives 8 and 9, respectively. Subjecting 5‐arylazo‐4‐methylmercapto‐3‐thiazolin‐2‐ones 8 to the action of aniline yields 5‐arylazo‐4‐phenylimino‐2‐thiazolidinones 10.