ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Tetrazole Compounds. 2. 1-Aryl-1H-tetrazole-5-acetaldehyde Derivatives from 1-Aryl-5-(2-dimethylamino-vinyl)-1H-tetrazoles1-Aryl-5-(2-dialkylamino-vinyl)-1H-tetrazoles 2, easily accessible by the reaction of 3-chloro-propeniminium salts 1 with excess sodium azide in refluxing alcohols, represent enamines of the hitherto unknown 1-aryl-1H-tetrazole-5-acetaldehydes 3. Attempts to isolate the latter after acid-catalyzed hydrolysis of 2 were unsuccessful. However, generated in situ, they can be trapped by suitable aldehyde reagents. Thus, starting from 1-aryl-5-(2-dimethylamino-vinyl)-1H-tetrazoles 4, the 4-nitrophenylhydrazones 5a--hyphen;i, 2,4-dinitrophenylhydrazones 5j--hyphen;r, and thiosemicarbazones 6 of the corresponding 1-aryl-1H-tetrazole-5-acetaldehydes 3 were obtained. Analogously, acid-catalyzed hydrolysis of 4 in the presence of 1,2-dianilinoethane resulted in 1-aryl-5-(1,3-diphenyl-2-imidazolidinylmethyl)-1H-tetrazoles 7. --hyphen; The structure of the aldehyde derivatives 5, 6, and 7 was proved by 1H n.m.r. spectroscopy.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19883300618
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