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Ringtransformationen von 3-substituiertem 5-Trifluormethyl-1,3,4-thiadiazol-2(3H)-on mit Nucleophilen

✍ Scribed by Haukur Kristinsson; Tammo Winkler; Max Mollenkopf

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
898 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Ring Transformations of 3‐Substituted 5‐Trifluoromethyl‐1,3,4‐thiadiazol‐2(3__H__)‐one with Nucleophiles

The 3‐chlormethyl‐5‐trifluoromethyl‐1,3,4‐thiadiazolone 3 undergoes a ring transformation to 3‐acylated 2,3‐dihydro‐1,3,4‐thiadiazoles 4 with many nucleophiles. Upon formal replacement of the chloromethyl group in the 3‐position of 3 by an extended bromoalkyl chain (→9a‐c), the reaction with nucleophiles yields 4‐acylated 5,6‐dihydro‐4__H__‐1,3,4‐thiadiazines 10 (from 9a), 4,5,6,7‐tetrahydrothiadiazepines 13 (from 9b) and 5,6,7,8‐tetrahydro‐4__H__‐1,3,4‐thiadiazocines 14 (from 9c) by ring enlargement. The 3‐propargyl‐thiadiazolone 17 rearranges with nucleophiles to 4‐acylated 6‐methylidene‐5,6‐dihydro‐4__H__‐1,3,4‐thiadiazines 18. The structures of the new compounds were elucidated by ^1^H‐ and ^13^C‐NMR spectroscopy.

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