Stereoselective domino assembling of five molecules: one-pot approach to $(2^\primeR^*,3S^*,4^\primeR^*)$-$2^\prime,4^\prime$-diaryl-$1^\prime,4^\prime$-dihydro-$2^\primeH $-spiro[indoline-$3,3^\prime$-pyridines]
A new stereoselective multicomponent reaction has been found: domino assembling of two equivalents of benzaldehyde, malononitrile, oxindole and excess of ammonium acetate in acetonitrile resulted in the formation of previously unknown $(2^\primeR^*,3S^*,4^\primeR^*)$-$6^\prime$-amino-2-oxo-$2^\prime...
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| Format: | Article |
| Language: | English |
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Académie des sciences
2020-06-01
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| Series: | Comptes Rendus. Chimie |
| Subjects: | |
| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.13/ |
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| author | Ryzhkov, Fedor V. Elinson, Michail N. Ryzhkova, Yuliya E. Vereshchagin, Anatoly N. Goloveshkin, Alexander S. Egorov, Mikhail P. |
| author_facet | Ryzhkov, Fedor V. Elinson, Michail N. Ryzhkova, Yuliya E. Vereshchagin, Anatoly N. Goloveshkin, Alexander S. Egorov, Mikhail P. |
| author_sort | Ryzhkov, Fedor V. |
| collection | DOAJ |
| description | A new stereoselective multicomponent reaction has been found: domino assembling of two equivalents of benzaldehyde, malononitrile, oxindole and excess of ammonium acetate in acetonitrile resulted in the formation of previously unknown $(2^\primeR^*,3S^*,4^\primeR^*)$-$6^\prime$-amino-2-oxo-$2^\prime,4^\prime$-diaryl-$1^\prime,4^\prime$-dihydro-$2^\primeH$-spiro[indoline-$3,3^\prime$-pyridine]-$5^\prime$-carbonitriles. Optimized reaction conditions and a mechanistic rationale for this multicomponent transformation are presented. This complex one-pot process occurs under mild conditions. The final compounds need no labor-intensive purification. |
| first_indexed | 2024-03-11T16:14:25Z |
| format | Article |
| id | doaj.art-a4d0d51f511d4694ac5385f2293bf699 |
| institution | Directory Open Access Journal |
| issn | 1878-1543 |
| language | English |
| last_indexed | 2024-03-11T16:14:25Z |
| publishDate | 2020-06-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj.art-a4d0d51f511d4694ac5385f2293bf6992023-10-24T14:22:41ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432020-06-0123215916810.5802/crchim.1310.5802/crchim.13Stereoselective domino assembling of five molecules: one-pot approach to $(2^\primeR^*,3S^*,4^\primeR^*)$-$2^\prime,4^\prime$-diaryl-$1^\prime,4^\prime$-dihydro-$2^\primeH $-spiro[indoline-$3,3^\prime$-pyridines]Ryzhkov, Fedor V.0Elinson, Michail N.1https://orcid.org/0000-0002-4647-5410Ryzhkova, Yuliya E.2Vereshchagin, Anatoly N.3https://orcid.org/0000-0001-8675-4943Goloveshkin, Alexander S.4Egorov, Mikhail P.5N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian FederationN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian FederationN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian FederationN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian FederationA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova 28, 119334, Moscow, Russian FederationN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian FederationA new stereoselective multicomponent reaction has been found: domino assembling of two equivalents of benzaldehyde, malononitrile, oxindole and excess of ammonium acetate in acetonitrile resulted in the formation of previously unknown $(2^\primeR^*,3S^*,4^\primeR^*)$-$6^\prime$-amino-2-oxo-$2^\prime,4^\prime$-diaryl-$1^\prime,4^\prime$-dihydro-$2^\primeH$-spiro[indoline-$3,3^\prime$-pyridine]-$5^\prime$-carbonitriles. Optimized reaction conditions and a mechanistic rationale for this multicomponent transformation are presented. This complex one-pot process occurs under mild conditions. The final compounds need no labor-intensive purification.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.13/MalononitrileOxindoleDomino reactionSpiro[indoline-33$^\prime$-pyridine]Knoevenagel condensationMichael addition |
| spellingShingle | Ryzhkov, Fedor V. Elinson, Michail N. Ryzhkova, Yuliya E. Vereshchagin, Anatoly N. Goloveshkin, Alexander S. Egorov, Mikhail P. Stereoselective domino assembling of five molecules: one-pot approach to $(2^\primeR^*,3S^*,4^\primeR^*)$-$2^\prime,4^\prime$-diaryl-$1^\prime,4^\prime$-dihydro-$2^\primeH $-spiro[indoline-$3,3^\prime$-pyridines] Comptes Rendus. Chimie Malononitrile Oxindole Domino reaction Spiro[indoline-3 3$^\prime$-pyridine] Knoevenagel condensation Michael addition |
| title | Stereoselective domino assembling of five molecules: one-pot approach to $(2^\primeR^*,3S^*,4^\primeR^*)$-$2^\prime,4^\prime$-diaryl-$1^\prime,4^\prime$-dihydro-$2^\primeH $-spiro[indoline-$3,3^\prime$-pyridines] |
| title_full | Stereoselective domino assembling of five molecules: one-pot approach to $(2^\primeR^*,3S^*,4^\primeR^*)$-$2^\prime,4^\prime$-diaryl-$1^\prime,4^\prime$-dihydro-$2^\primeH $-spiro[indoline-$3,3^\prime$-pyridines] |
| title_fullStr | Stereoselective domino assembling of five molecules: one-pot approach to $(2^\primeR^*,3S^*,4^\primeR^*)$-$2^\prime,4^\prime$-diaryl-$1^\prime,4^\prime$-dihydro-$2^\primeH $-spiro[indoline-$3,3^\prime$-pyridines] |
| title_full_unstemmed | Stereoselective domino assembling of five molecules: one-pot approach to $(2^\primeR^*,3S^*,4^\primeR^*)$-$2^\prime,4^\prime$-diaryl-$1^\prime,4^\prime$-dihydro-$2^\primeH $-spiro[indoline-$3,3^\prime$-pyridines] |
| title_short | Stereoselective domino assembling of five molecules: one-pot approach to $(2^\primeR^*,3S^*,4^\primeR^*)$-$2^\prime,4^\prime$-diaryl-$1^\prime,4^\prime$-dihydro-$2^\primeH $-spiro[indoline-$3,3^\prime$-pyridines] |
| title_sort | stereoselective domino assembling of five molecules one pot approach to 2 primer 3s 4 primer 2 prime 4 prime diaryl 1 prime 4 prime dihydro 2 primeh spiro indoline 3 3 prime pyridines |
| topic | Malononitrile Oxindole Domino reaction Spiro[indoline-3 3$^\prime$-pyridine] Knoevenagel condensation Michael addition |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.13/ |
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