Synthesis and Photocyclization of 1,2,4-Triazole-3-thiones

Sundararajan Aruna; Annamalai Senthilvelan; Dhakshanamurthy Thirumalai; Sengodagounder Muthusamy; Vayalakkavoor T. Ramakrishnan

doi:10.1055/s-2006-950301

PAPER

Synthesis and Photocyclization of 1,2,4-Triazole-3-thiones

Sundararajan Aruna^a, Annamalai Senthilvelan^a, Dhakshanamurthy Thirumalai^a, Sengodagounder Muthusamy^b, Vayalakkavoor T. Ramakrishnan*^a
^a Department of Organic Chemistry, School of Chemical Sciences, University of Madras, Guindy Campus, Chennai 600025, India
Fax: +91(44)22352494; e-Mail: vtrk28@yahoo.com;
^b Department of Chemistry, Bharathidasan University, Thiruchirappalli 620024, India

Abstract

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Abstract

Irradiation of thienyl and other substituted triazolothiones in a thin film reactor at 254 nm in an acetonitrile-dilute sodium hydroxide medium, furnished the respective triazolobenzothiazoles and, in some cases, the desulfurized product. The irradiation of anilinomethyl-, and aryloxymethyltriazolothiones under the above conditions also furnished the respective cyclized products and desulfurized compounds. Irradiation of benzyl substituted triazole thiones in the presence of triethylamine in benzene furnished the corresponding triazolothiazine and triazolodibenzazepine. Reaction of glycine hydrazide with aryl isothiocyanates furnished the triazolothiones, wherein glycine hydrazide functioned as a hydrazine-transferring agent. Irradiation of o-chlorophenyl substituted thione in basic acetonitrile medium furnished triazolodibenzdiazepine, whereas, the benzyl derivative furnished the triazolobenzothiazine.

Key words

photocyclization - photodesulfurization - triazoles - hydrazides - azepine

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