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Facile synthesis of 3-oxo-1,2,5-thiadiazoles; 7β-s̆ (3-oxo-1,2,5-thiadiazol-2-yl) cephalosporins

✍ Scribed by W.W.H. Lunn; J.K. Shadle

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
359 KB
Volume
48
Category
Article
ISSN
0040-4020

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✦ Synopsis

A simple pmcedure is described for the pqaration of 3-0x0-1.2,~~thiadbzoles under mild conditions. Thii procedure has provided hitherto unknown 7fL[3-ox~k1,2,5-tii1-2-y1] cephalosporins. N-Sulfinylamines, 1, have been shown to offer considerable synthetic opportunities.1~2~3 They have often been prepared by the reaction of thionyl chloride on the corresponding amines. More recently, Sakai and co-workers have used the action of sulfur dioxide on litbiated amines. Porskamp and Zwanenburg later found that sulfur dioxide and N-trimethylsilyl-lithioamines provided good yields of N-sulfinylamines.5 In this last procedure, the need for an excess of sulfur dioxide was stressed, this minimizing the formation of sulfurdiimines, 2. a-Aminoamides have been converted to 3-hydroxy-1.2.5~thiadiazoles 3 by sulfur monochloride, thionyl chloride or thionyl aniline69738 while the disubstituted 3-oxo-1,2,5-thiadiazolones 4 have been reported by

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