Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Understanding Chemistry and Unique NMR Characters of Novel Amide and Ester Leflunomide Analogues

Version 1 : Received: 29 November 2017 / Approved: 29 November 2017 / Online: 29 November 2017 (08:44:02 CET)

A peer-reviewed article of this Preprint also exists.

Henen, M.A.; Hamdi, A.; Farahat, A.A.; Massoud, M.A.M. Understanding Chemistry and Unique NMR Characters of Novel Amide and Ester Leflunomide Analogues. Magnetochemistry 2017, 3, 41. Henen, M.A.; Hamdi, A.; Farahat, A.A.; Massoud, M.A.M. Understanding Chemistry and Unique NMR Characters of Novel Amide and Ester Leflunomide Analogues. Magnetochemistry 2017, 3, 41.

Abstract

A series of diverse substituted 5-methyl-isoxazole-4-carboxylic acid amides, imide and esters of the formula (I) in which the benzene ring is mono or disubstituted was prepared. Spectroscopic and conformational examination was investigated and a new insight involving steric interference and interesting downfield deviation due to additional diamagnetic anisotropic effect of the amidic carbonyl group and the methine protons in 2,6-diisopropyl-aryl derivative (2) as a conformationaly restricted analogues Leflunomide was discussed. Individual substituent electronic effects through resonance of p-substituents and most stable conformation of compound (2) are discussed.

Keywords

Leflunomide derivatives, 2,6-diisopropylphenyl anilide chemical shift abnormalities, 5-methyl-4-isoxazole derivatives

Subject

Chemistry and Materials Science, Medicinal Chemistry

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