Thermal fragmentation and rearrangement of 2-(arylidenehydrazino)-4-(5H)-thiazolone derivatives: synthesis of 1,2,4-triazoles

Thermal fragmentation and rearrangement of 2-arylidenehydrazino-4-(5H)-thiazolone derivatives 1–3 led to the formation of 3-phenyl-1,2,4-triazole derivatives 11–13 as the major products in addition to 1-phenylphthalazine 15, 3-phenyl-2-thiohydantoin 19 and the corresponding nitriles, azines, thiogly...

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Bibliographic Details
Published in:Journal of analytical and applied pyrolysis 1998-03, Vol.45 (1), p.1-7
Main Authors: Gaber, Abd El-Aal M., Atalla, Ahmed A.
Format: Article
Language:English
Subjects:
1,2,4-Triazoles synthesis
4-(5H)-thiazolones
Pyrolysis
Rearrangement
Thermal fragmentation
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Summary:Thermal fragmentation and rearrangement of 2-arylidenehydrazino-4-(5H)-thiazolone derivatives 1–3 led to the formation of 3-phenyl-1,2,4-triazole derivatives 11–13 as the major products in addition to 1-phenylphthalazine 15, 3-phenyl-2-thiohydantoin 19 and the corresponding nitriles, azines, thioglycolic anilide 16 and thioglycolic acid 14. Thermal fragmentation of 1 in the presence of isoquinoline as a radical trap produced 1-phenylisoquinoline in addition to the previous products. A free radical mechanism has been suggested, involving the homolysis of C–S and C–N bonds to explain the isolated products.
ISSN:0165-2370
1873-250X
DOI:10.1016/S0165-2370(97)00086-7