New Application of 1,4-Dihydropyridine System: Michael Reactions Mediated by 1,4-Dihydropyridine-Enolate Adduct in Micellar Medium

Chemistry Letters

Volumn 32, Issue 11, 2003, Pages 1064-1065

  Mashraqui, Sabir H ^a   Karnik, Madhavi A ^a  

^a UNIVERSITY OF MUMBAI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROPYRIDINE; ACETOPHENONE DERIVATIVE; CETRIMIDE; PROTON; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; MICELLE; MICHAEL ADDITION; QUANTUM YIELD;

EID: 0842263686     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.1064     Document Type: Article

References (36)

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32. 2 gave only yield 13% of the corresponding Michael adduct after 36 h at room temperature, whereas no reaction occurred in acetonitrile solvent.
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34. -3 M, 100 mL) was added adduct 1 (180 mg, 0. 5 mmol), benzylidene acetophenone (1.04 g, 5 mmol) and acetyl acetone (550 mg, 5.5 mmol). The reaction mixture was stirred vigorously at room temperture for 8 h whereby the initial yellow color due to the starting chalcone diminished and a white, copious precipitate was formed. The reaction was filtered, and the solid product washed with 60% aqueous ethanol and air dried. Crystallisation from ethanol afforded the desired Michael product, 4-acetyl-1,3-diphenylhexane- 1,5-dione in 80% yield, mp 145-46°C (lit. mp 146°C; A. Garcia-Raso, B. Garcia-Raso, B. Campaner, R. Mestres, and J. V. Sinisterra, Synthesis, 1982, 1037). The preparation of adduct 1 is given as a supplementary information.
35. Structures of Michael adducts have been characterised by elemental analysis, IR and H-NMR spectral data.
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