High diastereoselective amine-catalyzed Knoevenagel–Michael-cyclization–ring-opening cascade between aldehydes, 3-arylisoxazol-5(4H)-ones and 3-aminocyclohex-2-en-1-ones

High diastereoselective amine-catalyzed Knoevenagel–Michael-cyclization–ring-opening cascade between aldehydes, 3-arylisoxazol-5(4H)-ones and 3-aminocyclohex-2-en-1-ones Full article

Journal

Molecular Diversity
ISSN: 1573-501X , E-ISSN: 1381-1991

Output data

Year: 2018, Volume: 22, Number: 3, Pages: 627-636 Pages count : 10 DOI: 10.1007/s11030-018-9817-4

Authors

Vereshchagin Anatoly N. ¹ , Elinson Michail N. ¹ , Anisina Yuliya E. ¹ , Karpenko Kirill A. ¹ , Goloveshkin Alexander S. ² , Zlotin Sergey G. ¹ , Egorov Mikhail P. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Moscow, Russian Federation

A highly diastereoselective three-component cascade reaction among aromatic aldehydes, 3-arylisoxazol-5(4H)-ones and 3-aminocyclohex-2-en-1-ones takes place under the catalysis of triethylamine, providing (3SR,4SR)-4-aryl-3-[(E)-(hydroxyimino)(aryl)methyl]-4,6,7,8-tetrahydroquinoline-2,5(1H,3H)-diones in 45–85% yields. The transformation presumably proceeds through a sequential cascade of Knoevenagel/Michael-addition/cyclization/ring-opening reactions. This process was carried out in green media (EtOH/water, 1:1–1:3) at reflux. Products are crystallized directly from the reaction mixture and their isolation includes only filtration. The structure of (3SR,4SR)-3-[(E)-(hydroxyimino)(phenyl)methyl]-7,7-dimethyl-4-phenyl-4,6,7,8-tetrahydroquinoline-2,5(1H,3H)-dione was confirmed by X-ray diffraction analysis.

Vereshchagin A.N. , Elinson M.N. , Anisina Y.E. , Karpenko K.A. , Goloveshkin A.S. , Zlotin S.G. , Egorov M.P.
High diastereoselective amine-catalyzed Knoevenagel–Michael-cyclization–ring-opening cascade between aldehydes, 3-arylisoxazol-5(4H)-ones and 3-aminocyclohex-2-en-1-ones
Molecular Diversity. 2018. V.22. N3. P.627-636. DOI: 10.1007/s11030-018-9817-4 WOS Scopus OpenAlex

Web of science:	WOS:000441550000008
Scopus:	2-s2.0-85046040505
OpenAlex:	W2792932189

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