Interaction of maleimides and itaconimides with carboxymethyleneazine binucleophiles

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Abstract

The nature of the interaction of N-arylmaleimides and N-arylitaconimides with some carboxymethyleneazines has been studied. The reaction of itaconic acid imides with oxopiperazinylidene acetates and oxomorpholinylidene acetate leads to imide recyclization and the formation of pyridine-containing heterosystems. The interaction of N-arylitaconimides and N-arylmaleimides with oxoquinoxalinylidene acetate involves Michael addition with the formation of linear adducts. The features of this process have been substantiated using quantum-chemical calculations.

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About the authors

Ya. Y. Kulichikhina

Voronezh State University

Author for correspondence.
Email: shmoylovay@gmail.com
ORCID iD: 0000-0003-0818-9920
Russian Federation, Universitetskaya pl., 1, Voronezh, 394018

S. M. Medvedeva

Voronezh State University

Email: shmoylovay@gmail.com
ORCID iD: 0000-0003-0236-9197
Russian Federation, Universitetskaya pl., 1, Voronezh, 394018

I. V. Nechaev

Voronezh State University

Email: shmoylovay@gmail.com
ORCID iD: 0000-0002-1232-8869
Russian Federation, Universitetskaya pl., 1, Voronezh, 394018

Yu. A. Kovygin

Voronezh State University

Email: shmoylovay@gmail.com
ORCID iD: 0000-0001-5286-2874
Russian Federation, Universitetskaya pl., 1, Voronezh, 394018

М. A. Present

Zelinsky Russian Academy of Sciences

Email: shmoylovay@gmail.com
ORCID iD: 0000-0002-1164-9652
Russian Federation, Leninsky prosp., 4, Moscow, 119991

D. V. Nikitenko

Russia сInstitute of Physical Organic Chemistry and Coal Chemistry

Email: shmoylovay@gmail.com
ORCID iD: 0000-0001-6902-8114
Russian Federation, ul. Rosy Luxemburg, 70, Donetsk, 283048

Kh. S. Shikhaliev

Voronezh State University

Email: shmoylovay@gmail.com
ORCID iD: 0000-0002-6576-0305
Russian Federation, Universitetskaya pl., 1, Voronezh, 394018

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Supplementary files

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2. Scheme 1

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3. Scheme 2

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4. Scheme 3

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5. Fig. 1. Tautomeric forms of alkyl 2-(3-oxopiperazin-2-ylidene)acetates 3 (a) and 3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidenemethyl acetate 4 (b)

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6. Fig. 2. The values ​​of the atomic charges of the molecules of methyl 2-(3-oxopiperazin-2-ylidene)acetate 3a (a) and 3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidenemethyl acetate 4 (b)

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7. Fig. 3. Structure of the HOMO of methyl (3-oxopiperazin-2-ylidene)acetate 3a

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8. Fig. 4. The structure of the HOMO of methyl (3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)acetate 4a

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9. Fig. 5. Structure of LUMO of N-phenylitaconimide 1a

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10. Fig. 6. The most significant correlations in the HMBC 1H–13C spectrum of methyl 3-(1-(4-nitrophenyl)-2,5-dioxopyrrolidin-3-yl)-2-(3-oxo-3,4-dihydroquinoxalin-2-yl)propanoate 10b (a) and the alternative methyl 9-(2-((4-nitrophenyl)amino)-2-oxoethyl)-6,10-dioxo-6,8,9,10-tetrahydro-5H-pyrido[1,2-a]quinoxaline-7- carboxylate 11b (b)

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11. Fig. 7. The values ​​of atomic charges of methyl 3-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-(3-oxo-3,4,5,6-tetrahydropyrazin-2-yl)propanoate molecules int-7h (a) and methyl 3-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-(3-oxo-3,4-dihydroquinoxalin-2-yl)propanoate 10h (b)

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12. Fig. 8. The most significant correlations in the NOESY spectrum 1H–1H of ethyl 2-(2,5-dioxo-1-(p-tolyl)pyrrolidin-3-yl)-2-(3-oxo-3,4-dihydroquinoxalin-2-yl)acetate 13e

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13. Figure

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