Synthesis, Table of Contents SHORTPAPER © Georg Thieme Verlag Stuttgart · New York Synthesis of 1,3,4-Thiadiazoles from Aldehyde Hydrazones Kentaro Okuma*, Kazuko Nagakura, Yasutaka Nakajima, Kento Kubo, Kosei ShiojiDepartment of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-0180, JapanFax: +81(92)8656030; e-Mail: kokuma@fukuoka-u.ac.jp; Recommend Article Abstract Buy Article All articles of this category Abstract Reaction of p-tolualdehyde hydrazone with disulfur dichloride in the presence of DBU gave 2,5-di (p-tolyl)-1,3,4-thiadiazole (1a) in 54% yield. Phenyldiazomethane also reacted with disulfur dichloride to afford 2,5-diphenyl-1,3,4-thiadiazole (1b) in 80% yield. Key words hydrazone - disulfur dichloride - 1,3,4-thiadiazole - phenyldiazomethane Full Text References References For reviews, see: 1a Wilkins DJ. Bradley PA. In Progress in Heterocyclic Chemistry Vol. 14: Gribble GW. Joule JA. Pergamon Press; Oxford UK: 2002. p.214-218 1b Banbas LL. The Chemistry of Heterocyclic Compounds Wiley-Interscience; New York: 1952. p.81-134 2 Jensen KA. Pederson C. Acta Chem. Scand. 1961, 15: 1124 3 Huisgen R. Strurumu HJ. Seidel M. Chem. Ber. 1961, 94: 1555 4 Le V.-D. Rees CW. Sivadasan S. J. Chem. Soc., Perkin Trans. 1 2002, 1543 5 Rusmussen PB. Pedersen U. Thompson I. Yde BS. Lawesson O. Bull. Soc. Chim. Fr. 1985, 62 6 Linganna N. Lokanatha KM. Synth. Commun. 1998, 28: 4611 7a Okazaki R. Inoue K. Inamoto N. Tetrahedron Lett. 1979, 3673 7b Okazaki R. Inoue K. Inamoto N. Bull. Chem. Soc. Jpn. 1981, 54: 3541 8 Okuma K. Kubo K. Yokomori Y. Heterocycles 2003, 60: 299 9 Creary X. Org. Synth. 1986, 64: 207 10 Hinman RL. J. Org. Chem. 1960, 26: 1775 11 Barton DHR. Guziec FS. Shahak I. J. Chem. Soc. 1974, 1794 12a Staudinger H. Siegert J. Helv. Chim. Acta 1920, 3: 833 12b Schönberg A. Vargha L. Liebigs Ann. Chem. 1930, 483: 176 12c Kalwinski I. Li X. Gottstein J. Huisgen R. J. Am. Chem. Soc. 1981, 103: 7032 13 Mazzonne G. Puglisi G. Bonina F. Corsaro A. J. Heterocycl. Chem. 1983, 20: 1399 14 Tsuge O. Kanemasa S. Bull. Chem. Soc. Jpn. 1972, 45: 3591 15 Rosini G. Soverini M. Ballini R. Synthesis 1983, 909 16 Flowers WT. Robinson JF. Taylor DR. Tipping AE. J. Chem. Soc., Perkin Trans. 1 1981, 349 17 Chattopadhyaya JB. Rao AVR. Ind. J. Chem. 1975, 13: 632 18 Tsuge O. Tashiro M. Hokama K. Nippon Kagaku Zasshi 1969, 90: 572 ; Chem. Abstr. 1969, 71, 49060 19 Nyquist RA. Peters TL. Buude PB. Spectrochim. Acta, Part A 1978, 34A: 503
