Synthesis of 4-{[(2Z)-4-Aryl-1-methoxy-1,4-dioxobut-2-en-2-yl]amino}benzoic acids and their reaction with ninhydrin

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4-{[(2Z)-4-Aryl-1-methoxy-1,4-dioxobut-2-en-2-yl)]amino}benzoic acids were synthesized by reaction methyl esters of aroylpyruvic acids with 4-aminobenzoic (para-aminobenzoic) acid in a mixture of glacial acetic acid–ethanol, 1:1. The obtained compounds reacted with ninhydrin in glacial acetic acid to form 4-{3-aroyl-1ʹ,3ʹ-dihydro-1ʹ,3ʹ,5-trioxo-5H-spiro[furan-2,2ʹ-indan]-4-yl)amino}benzoic acids. The structure of the obtained compounds was determined using IR, NMR 1H and13C{1H} spectroscopy and X-ray crystallography.

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作者简介

V. Gein

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

编辑信件的主要联系方式.
Email: geinvl48@mail.ru
ORCID iD: 0000-0002-8512-0399
俄罗斯联邦, 614990, Perm

D. Chalkov

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: geinvl48@mail.ru
ORCID iD: 0009-0001-0367-3863
俄罗斯联邦, 614990, Perm

O. Bobrovskaya

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: geinvl48@mail.ru
ORCID iD: 0000-0002-3394-9031
俄罗斯联邦, 614990, Perm

M. Dmitriev

Perm State National Research University

Email: geinvl48@mail.ru
ORCID iD: 0000-0002-8817-0543
俄罗斯联邦, 614990, Perm

参考

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2. Scheme 1. R = C6H5 (1a), 4-MeC6H4 (1b), 4-MeOC6H4 (1c), 4-EtOC6H4 (1d), 4-FC6H4 (1e), 4-ClC6H4 (1f), 2,4-(Cl)2C6H3 (1g), 4-BrC6H4 (1h), 4-NO2C6H4 (1i), 3-NO2C6H4 (1j).

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3. Scheme 2. R = C6H5 (2a), 4-MeC6H4 (2b), 4-MeOC6H4 (2c), 4-EtOC6H4 (2d), 4-FC6H4 (2d), 4-ClC6H4 (2e), 2,4-(Cl)2C6H3 (2g), 4-BrC6H4 (2h), 4-NO2C6H4 (2i), 3-NO2C6H4 (2j).

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4. Fig. 1. General view of the molecule of compound 2a according to X-ray diffraction data, represented by thermal ellipsoids of 30% probability.

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