Preparation of novel 1,2,4-thiadiazoles by cyclization with 4-methylbenzenesulfonyl cyanide (tosyl cyanide)

The preparation of 1,2,4-thiadiazoles with a di-tert-butylphenol substituent at the thiadiazole 3-position is described. A thermally generated nitrile sulfide was reacted with tosyl cyanide in a 1,3-dipolar cyclization reaction to provide a thiadiazole intermediate containing a labile 5-tosyl substituent.

[1]  R. D. Dyer,et al.  Novel 1,2,4-oxadiazoles and 1,2,4-thiadiazoles as dual 5-lipoxygenase and cyclooxygenase inhibitors. , 1992, Journal of medicinal chemistry.

[2]  G. L'abbé,et al.  Cycloaddition-elimination reactions of Freund's methyl isothiocyanate sulfide with electrophilic nitriles , 1991 .

[3]  G. L'abbé,et al.  Cycloaddition-elimination reactions of 4-methyl-5-phenylimino-Δ2-1,2,3,4-thiatriazoline with electrophilic nitriles , 1991 .

[4]  D. Ortwine,et al.  Styrylpyrazoles, styrylisoxazoles, and styrylisothiazoles. Novel 5-lipoxygenase and cyclooxygenase inhibitors. , 1991, Journal of medicinal chemistry.

[5]  R. Paton.  The chemistry of nitrile sulphides , 1989 .

[6]  R. Schleyerbach,et al.  Substituted 3-phenyl-7H-thiazolo(3,2-b)(1,2,4)triazin-7-ones as antiinflammatory agents with immunomodulating properties. , 1989, Drugs under experimental and clinical research.

[7]  R. Beaudegnies,et al.  A Diels-Alder route towards pyrimidin-4-ones , 1988 .

[8]  H. Homma,et al.  Synthesis and anti-inflammatory activity of 2,6-di-tert-butylphenols with a heterocyclic group at the 4-position. III. , 1984, Chemical & pharmaceutical bulletin.

[9]  J. E. Franz,et al.  4.25 – 1,2,4-Thiadiazoles , 1984 .

[10]  S. Weinreb,et al.  Synthetic aspects of diels-alder cycloadditions with heterodienophiles , 1982 .

[11]  W. C. Still,et al.  Rapid chromatographic technique for preparative separations with moderate resolution , 1978 .

[12]  R. Howe,et al.  Nitrile sulfides. Synthesis of 1,2,4-thiadiazoles , 1974 .

[13]  L. Cohen.  Electronic Control of Steric Hindrance in Hindered Phenols1 , 1957 .