ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Whereas treatment of 2-butyloxy-, 2-pentyloxy- and 2-β-phenylethyloxy-4-arylazo-2-thiazolin-5-ones 1d-h with strong basic amines results in their rearrangement into 1-aryl- Δ2-1,2,4-triazolin-5-one-3-carboxylic acid derivatives 2, the 2-isobutyloxy, 2-(2-octyloxy)- and the 2-cyclohexyloxy-4-arylazo-2-thiazoline-5-ones 1i-n rearrange upon treatment with the same reagents into Δ2- 1,2,4-triazoline-5-thione-3-carboxylic acid derivatives 3. On the other hand, 1d-h,1 react with aromatic amines to give 1-aryl-2-alkoxy-1,2,4-triazole-3-carboxylic acid anilides 4a-i, via the loss of hydrogen sulphide. The phenylhydrazides 4j-l are obtained upon treatment of 1g, h,l with phenylhadrazine.Treatment of 4-arylidene-2-benzylmercapto-2-thiazolin-5-ones 6a-c with ammonia results in the formation of the thiohydantoin derivatives 7e, g. However, 6b, c react with phenylhydrazine to yield the phenylhydrazides 8b, c.The reaction of 6a-e with piperidine or morpholine involves to molecules of the reagent to yield 10a-d which are thermally cyclised to the thiazolone derivatives 11a-d.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19733150204
Permalink
