Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2004(12): 1929-1931
DOI: 10.1055/s-2004-829156
DOI: 10.1055/s-2004-829156
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of 1,3,4-Thiadiazoles from Aldehyde Hydrazones
Further Information
Received
18 March 2004
Publication Date:
21 July 2004 (online)
Publication History
Publication Date:
21 July 2004 (online)

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
- 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