Synthesis and stereochemical structure of derivatives of 2-substituted 3-cyclohexenylamidoquinazolin-4-ones obtained from N′-cyclohexenecarbonyl-substituted hydrazides of 2-aminobenzoic acid and certain orthoesters

Abstract

In the reaction of N′-cyclohexenecarbonyl-substituted hydrazides of 2-aminobenzoic acid with the trialkyl esters of formic, acetic, valeric, and benzoic acids at room temperature 3-cyclohexenylamidoquinazolin-4-ones with the respective substituent at the C-2 atom of the quinazoline ring were obtained. The spatial structure of the obtained compounds was studied by homonuclear and heteronuclear NMR.In a continuation of researches on the synthesis of quinazolinone derivatives [1, 2], among which substances with sedative activity on the central nervous system [3,4], anticonvulsive activity [5], and antiallergic activity [6] were found, this article sets out the results of investigations into the synthesis of 2-substituted 3-cyclohexenylamidoquinazolinones, which have not been described in the literature, in the reactions of N′-cyclohexenecarbonyl-substituted 2-aminobenzohydrazides 1a,b with certain orthoesters 2-5. NH 2 N H O N H O R HOOC Me N O N H O R Me N R 1 R 2 R 1 C(OAlk) 3 2-5 1a,b 6a,b-13a,b1, 6-13 a R = H, b R = F; 2, 3 Alk = Et, 4, 5 Alk = Me; 2, 6, 10 R 1 = H, 3, 7, 11 R 1 = Me, 4, 8, 12 R 1 = (CH 2 ) 3 Me, 5, 9, 13 R 1 = Ph; 6-9 R 2 = COOH, 10-13 R 2 = H __________________________________________________________________________________________