1,3-dipolar cycloaddition as a method for the synthesis of dipyrrolidinyl- and dipyrrolylketones

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Abstract

In the reactions of 1,3-dipolar cycloaddition of a twofold excess of aryl aldimines of glycine ethyl ester with diarylideneacetones and diarylidenecyclohexanones in the presence of silver acetate, the corresponding dipyrrolidinylketones were obtained. Diethyl 4,4′-carbonylbis(3,5-diarylpyrrolidine-2-carboxylates) obtained from diarylideneacetones undergo aromatization under the action of N-bromosuccinimide to form diethyl 4,4′-carbonylbis(3,5-diaryl-1H-pyrrole-2-carboxylates). The selectivity of the reactions and the structure of the products were determined using correlation NMR spectroscopy and X-ray diffraction analysis.

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About the authors

S. G. Kostryukov

National Research Ogarev Mordovia State University

Author for correspondence.
Email: kostryukov_sg@mail.ru
ORCID iD: 0000-0002-1774-0836
Russian Federation, Saransk, 430005

V. A. Kalyazin

National Research Ogarev Mordovia State University

Email: kostryukov_sg@mail.ru
ORCID iD: 0000-0002-0650-6753
Russian Federation, Saransk, 430005

P. S. Petrov

National Research Ogarev Mordovia State University

Email: kostryukov_sg@mail.ru
ORCID iD: 0000-0001-7232-0335
Russian Federation, Saransk, 430005

E. V. Bezrukova

National Research Ogarev Mordovia State University

Email: kostryukov_sg@mail.ru
ORCID iD: 0000-0003-2428-3925
Russian Federation, Saransk, 430005

N. V. Somov

Lobachevsky State University of Nizhny Novgorod

Email: kostryukov_sg@mail.ru
ORCID iD: 0000-0001-9460-307X
Russian Federation, Nizhnij Novgorod, 603950

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Supplementary files

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1. JATS XML
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2. Fig. 1. Spatial structure (2S*,2'S*,3R*,3'R*, 4S*,4'S*,5R*,5'R*)-diethyl-4,4'-carbonylbis(5-phenyl-3-(4-chlorophenyl)pyrrolidine-2-carboxylate) 6a according to the RSA.Fig. 1. Spatial structure (2S*,2'S*,3R*,3'R*, 4S*,4'S*,5R*,5'R*)-diethyl-4,4'-carbonylbis(5-phenyl-3-(4-chlorophenyl)pyrrolidine-2-carboxylate) 6a according to the RSA.

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3. Fig. 2. Fragment of the 1H–13C HMBC spectrum (2S*,2'S*,3R*,3'R*,4S*,4'S*,5R*,5'R*)-диэтил-4,4'-карбонилбис[3,5-бис(4-хлорфенил)пирролидин-2-карбоксилата] 6b.

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4. Fig. 3. Fragment of the 1H–1H NOESY spectrum (2S*,2'S*,3R*,3'R*,4S*,4'S*,5R*,5'R*)-диэтил-4,4'-карбонилбис[3,5-бис(4-хлорфенил)пирролидин-2-карбоксилата] 6b.

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5. Fig. 4. Fragment of the spectrum of 1H–13C HMBC (1S*,3S*,4S*,5S*,7S*,8S*,10S*,11S*)-diethyl-6-oxo-1,8-diphenyl-4,11-bis- (4-chlorophenyl)-2,9-diazadispiro[4.1.47.35]tetradecane-3,10-carboxylate 12a.

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6. Fig. 5. Fragment of the spectrum of 1H–1H NOESY (1S*,3S*,4S*,5S*,7S*,8S*,10S*,11S*)-diethyl-6-oxo-1,8-diphenyl-4,11-bis- (4-chlorophenyl)-2,9-diazadispiro[4.1.47.35]tetradecane-3,10-carboxylate 12a.

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7. Fig. 6. Fragment of the spectrum of 1H–1H NOESY (1S*,3S*,4S*,5S*,E)-ethyl-6-oxo-1-phenyl-7-(4-chlorobenzylidene)-4-(4-chlorophenyl)-2-azaspiro[4.5]Decan-3-carboxylate 14.

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8. Fig. 7. A fragment of the 1H–1H NOESY spectrum of compounds 14 and 14' (signals and cross-peaks for compound 14' are indicated).

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9. Scheme 1.

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10. Scheme 2.

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11. Scheme 3.

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12. Scheme 4.

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13. Scheme 5.

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14. Scheme 6.

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15. Scheme 7.

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16. Scheme 8.

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