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Synthesis and thermolysis of the 2,3-dihydro-1H-pyrole-2,3-diones, pseudopericyclic reactions of formyl(N-phenylimidoyl)ketene: Experimental data and PM3 calculations

✍ Scribed by Emin Saripinar; Süleyman Karataş

Book ID
102343968
Publisher
Journal of Heterocyclic Chemistry
Year
2005
Tongue
English
Weight
315 KB
Volume
42
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reactions of the 2,3‐dihydro‐1__H__‐furan‐2,3‐dione 1 with Schiff bases 2a‐f at 60–70°C furnish the corresponding 2,3‐dihydro‐1__H__‐pyrole‐2,3‐diones 3a‐f. The heating of 3a‐d afforded the corresponding 4‐methoxybenzoyl(N‐arylimidoyl)k:etenes 4a‐d as intermediates which undergo a very facile cyclization to quinoline‐4‐ones 5a‐d. According to our PM3 calculations, fragmentation of 4‐formyl‐2,3‐dihydro‐1__H__‐pyrole‐2,3‐dione and 1,4‐cyclization of formyl(N‐phenylimidoyl)k:etene IN1 to azetin‐2‐one IN2 and oxe‐tone IN3 are pseudopericyclic reactions with two orbital connections, proceed via planar transition structures. Due to to the possibility of syn and anti conformations of the imine phenyl, there are eight E/Z‐iso‐mers of IN1. In addition, we have also calculated reaction mechanism of formation of quinoline‐4‐ones by the PM3 method.

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