Synthesis of potential plant protecting compounds on the basis of 2,3-dihydrothiazol-2-thione. III. Structural variations by reactions of the thiocarbonyl group

The 2.3-dihydrothiazol-2-thiones 1a-c have been methylated to the 2-methyls ulfanylthiazolium iodides 2a-c, which could be reacted with double activate d CII-acidic compounds like 4-nitrophenylacetonitrile (3) to yield 5 and 6a ,b, with malonic acid derivatives 7a-c to yield the push-pull substituted k etene-S.N-acetales 8a-c or with 3-aminorhodanine derivatives to yield 12a,b . Vinylogous CH-acidic compounds like 9a-d reacted with 2b to the push-pull substituted butadienes 10a-d. With p-phenethidine 2b formed depending on t he reaction conditions either the rare structure of an ortho-dithiocarbonic diester diamide (14) or the isothiourea 15. With hydrazino compounds, 16a- c with hydrazono partial structure resulted. Efforts to acylate the unsubst ituted nitrogen of 17 with carbonic acid ester derivatives always yielded t he S-acylated products 18 and 20a,b.