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Boulton-Katritzky Rearrangement of 5-(cyanoimino)-1,2,4-Thiadiazolines

✍ Scribed by Sonnenschein, Helmut ;Schmitz, Ernst ;Gründemann, Egon ;Schröder, Edith

Book ID
102367297
Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
376 KB
Volume
1994
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The products of the addition of nucleophiles (alcohols, amines) to the cyano group of 5‐(cyanoimino)thiadiazolines 1 undergo a Boulton‐Katritzky rearrangement. The thiadiazoles 4 are formed by subsequent nitrile elimination. In the case of bicyclic thiadiazoloazepine 5 an equilibrium mixture of unrearranged iminothiadiazoline 6 and rearranged thiadiazole 7 is obtained as an intermediate.

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## Abstract magnified image Isocarboxazid rearranges on heating to 5‐acetonyl‐2‐benzyl‐4‐hydroxy‐1,2,3‐triazole in DMF at 150°C, in the ionic liquid, [bmin]HSO at 100°C or as a melt at 105°C. This is the first reported example of the Boulton–Katritzky rearrangement of an acyl hydrazide. J. Heteroc