CONTRIBUTIONS TO THE CHEMISTRY OF ENAMINO KETONES .15. THE 3-COMPONENT SYNTHESIS OF HYDRAZIDOMETHYLENE-CHROMANDIONES AND A REDUCTIVE N-N BOND-CLEAVAGE OF PHENYLHYDRAZINE

Authors
JUNEK H REIDLINGER C
Citation
H. Junek et C. Reidlinger, CONTRIBUTIONS TO THE CHEMISTRY OF ENAMINO KETONES .15. THE 3-COMPONENT SYNTHESIS OF HYDRAZIDOMETHYLENE-CHROMANDIONES AND A REDUCTIVE N-N BOND-CLEAVAGE OF PHENYLHYDRAZINE, Monatshefte fuer Chemie, 126(5), 1995, pp. 579-586
Citations number
30
Categorie Soggetti
Chemistry
Journal title
Monatshefte fuer Chemie → ACNP
ISSN journal
00269247
Volume
126
Issue
5
Year of publication
1995
Pages
579 - 586
Database
ISI
SICI code
0026-9247(1995)126:5<579:CTTCOE>2.0.ZU;2-L
Abstract
The three-component reaction of 4-hydroxycoumarin, ethylorthoformiate, and different substituted hydrazines is described. p-Nitrophenylhydra zine, hydrazides and phenylsemicarbazide lead to the expected hydrazin omethylene-chromandiones 2a-f. Reaction of 4-hydroxycoumarin, ethylort hoformiate, and phenylhydrazine or p-tolyl-hydrazine does not yield 2, but the anilino-methylene-chromandiones 6a-b. This indicates a reduct ive N-N bond cleavage to aniline and ammonia under mild conditions.