It has been well proved that various derivatives of 2-hydroxybenzoic acid (salicilic acid) exhibit strong antimicrobial activity [1]. Among others same halogenated salicilanilides show high antifungal action [2]. Undertaking studies in that research field we have synthesized a series of novel S-esters and S,S'-diesters of N'-(2-hydroxybenzoyl), N'-(2,4-dihydroxybenzoyl), and N'-(5-chloro-2-hydroxybenzoyl)  hydrazinecarbodithioic acid. Methyl esters 1-3 of appropriate carboxylic acids led to hydrazides 4-6 and N'-methylhydrazides 7-9 while treated with hydrazine hydrate or methylhydrazine. Hydrazides 4-6 applied to the reaction with carbon disulfide and appropriate halides in the presence of triethylamine gave cyclic 1,3-dithiolane and 1,3-dithiane derivatives 10-15, S-esters 16, 17 and S,S'-diesters 25-34 while N'-methylhydrazides 7-9 reacted to S-esters 18-24. In two cases 1,3,4-oxadiazole-5-thiones 35, 36 were formed in side reactions.

References:

[1] H. Lamaire, C.H. Schramm, A. Cahn, J. Pharm. Sci. 50, 1961, 831-832.

[2] J. Vinsova, A. Imramovsky, V. Buchta, M. Ceckova, M. Dolezal, F. Staud, J. Jampelek, J. Kaustova, Molecules 12, 2007, 1-12.

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