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Synthesis 2006(22): 3841-3848  
DOI: 10.1055/s-2006-950301
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Sundararajan Arunaa, Annamalai Senthilvelana, Dhakshanamurthy Thirumalaia, Sengodagounder Muthusamyb, 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
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Publication History

Received 20 June 2006
Publication Date:
09 October 2006 (online)

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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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