ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Tetrazole Compounds. 5. Synthesis and Transamination of Enamino Ketones of the Tetrazole SeriesTetrazole-5-acetaldehyde enamines 5 react with aliphatic and aromatic carboxylic acid chlorides in the presence of an auxiliary base (e.g. pyridine or triethylamine) to give tetrazolylsubstituted enamino ketones 6. The latter can be modified by acid-catalyzed transamination with secondary aliphatic amines (e.g. diethylamine, pyrrolidine, piperidine, morpholine, hexamethylene imine) yielding 5-(1-acyl-2-dialkylamino-vinyl)-1-aryl-1 H-tetrazoles 7. The analogue transamination of 6 with primary alkyl, aralkyl, and aryl amines results in corresponding secondary enamino ketones 8, which exist in solution as an equilibrium mixture of the Z and E form. Acylation of secondary tetrazole-5-acetaldehyde enamines 9 does not lead to 8, but to the isomeric N-acyl derivatives 10. - Characteristic 1H-n.m.r., u.v., and i.r. spectroscopic data of the novel products are reported.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19903320615
