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A convenient synthesis of 1,2-dihydro-1,2,4-triazolo[3,2-b]quinazolin-9(1H)-ones and their 1,2,4-triazolo derivatives

El-Hiti, Gamal A. 1997. A convenient synthesis of 1,2-dihydro-1,2,4-triazolo[3,2-b]quinazolin-9(1H)-ones and their 1,2,4-triazolo derivatives. Bulletin of the Chemical Society of Japan 70 (9) , pp. 2209-2213. 10.1246/bcsj.70.2209

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Abstract

A range of l,2-dihydro-l,2,4-triazolo[3,2-b]quinazolin-9(lH)-ones (3) has been synthesized in very good yields by the reaction of 3-amino-2-anilino-4(3H)-quinazolinone (1) with aromatics aldehydes in the presence of excess piperidine as a base. The l,2,4-triazolo[3,2-b]quinazolin-9(lH)-ones could be obtained in very good yields by dehydrogenation of compounds 3 with thionyl chloride. Reaction of 1 with active methylene compounds (diethyl malonate and acetylacetone) resulted in the production of condensed products. These condensed products could be cyclized to l,2,4-triazolo[3,2-fc]quinazolin-9(lH)-one by heating above the melting point. Acetylation of 1 by acetic anhydride was found to be dependent on the reaction conditions. The acetyl derivative 3-acetamido-2-anilino-4(3H)-quinazolinone formed under mild conditions, while dimerization took place under strong conditions to give a pentacyclic compound in very good yield.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Chemical Society of Japan
ISSN: 0009-2673
Last Modified: 19 Mar 2016 22:25
URI: http://orca-mwe.cf.ac.uk/id/eprint/15624

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