Competitive Cyclization in the Reaction of Hexafluoropropene with 2-Aminobenzamide
- 1 November 1977
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 50 (11) , 3014-3017
- https://doi.org/10.1246/bcsj.50.3014
Abstract
The reaction of hexafluoropropene(HFP) with 2-aminobenzamide afforded 2-(1,2,2,2-tetrafluoroethyl)-4(3H)-quinazolinone (4) and N-(2-cyanophenyl)-2,3,3,3-tetrafluoropropionamide (5) in ca.1 : 1 ratio, which is essentially independent of the reaction temperatures ranging from room temperature to 100 °C. The formation of the two products is explained in terms of the competitive cyclization of the imidoyl fluoride intermediate, the N-6 and O-6 ring closures ultimately yielding 4 and 5, respectively. In contrast to the HFP reaction, 2-(trifluoromethyl)pentafluoropropene (OFIB) and 2-aminobenzamide gave only the O-6 cyclized product, N-(2-cyanophenyl)-2-trifluoromethyl-3,3,3-trifluoropropionamide. The difference in reactivity between HFP and OFIB is discussed.This publication has 5 references indexed in Scilit:
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