ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Tetrazole Compounds. 3. Modification of 1-Aryl-1H-tetrazole-5-acetaldehyde Enamines by Acid-Catalyzed TransaminationThe acid-catalyzed transamination of tetrazole-5-acetaldehyde enamines proves to be a useful synthetic method for preparing specially N-substituted enamines of this series not accessible directly from 3-chloro-propeniminium salts 3 and sodium azide. Thus, starting from (E)-1-aryl-5-(2-dimethylamino-vinyl)-1H-tetrazoles 5 transamination with dialkylamines yields tertiary enamines of types 6 and 7. Analogously, acid-catalyzed reaction of 5 with N-alkylanilines leads to 1-aryl-5-[2-(N-alkylanilino)-vinyl]-1H-tetrazoles 8. Bifunctinal secondary amines such as N,N′-dimethylethylenediamine result in systems of type 9 with two linked tertiary tetrazolyvinylamino groups. All the transaminations with secondary amines proceed with retention of configuration. According to the same reaction scheme transamination of 5 (Ar = Ph) with primary alkyl-, aralkyl-, and arylamines affords secondary tetrazolylvinylamines 10; however, here the formation of Z-configurated products dominates. Bifunctional primary amines like ethylenediamine and 1,2-phenylenediamine react with 5 to give the N,N′-linked systems 11 and 12 possessing two secondary tetrazolylvinylamino groups. - Characteristic i.r., u.v., and 1H-n.m.r. spectroscopic data of the novel tetrazole-5-acetaldehyde enamines are reported.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19883300619
