ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Ring Transformations of 3-Substituted 5-Trifluoromethyl-1,3,4-thiadiazol-2(3H)-one with NucleophilesThe 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-4H-1,3,4-thiadiazines 10 (from 9a), 4,5,6,7-tetrahydrothiadiazepines 13 (from 9b) and 5,6,7,8-tetrahydro-4H-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-4H-1,3,4-thiadiazines 18. The structures of the new compounds were elucidated by 1H- and 13C-NMR spectroscopy.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19830660841
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