Silicon tetrachloride catalyzed aza-michael addition of amines to conjugated alkenes under solvent-free conditions

Synlett

Volumn , Issue 3, 2010, Pages 379-382

  Azizi, Najmedin ^a   Baghi, Roya ^b   Ghafuri, Hossein ^b   Bolourtchian, Mohammad ^a   Hashemi, Mohammad ^b  

^a CHEMISTRY AND CHEMICAL ENGINEERING RESEARCH CENTER OF IRAN   (Iran)

^b SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

aminocarbonyl compounds; Aromatic amine; Conjugate addition; Silicon tetrachloride

Indexed keywords

ALKENE DERIVATIVE; ALKYL GROUP; AMINE; AROMATIC AMINE; CARBONYL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILICON; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; CONJUGATION; MICHAEL ADDITION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 76249094658     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219195     Document Type: Article

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54. To the mixture of amine (5 mmol) and Michael acceptor (5.2 mmol) under argon, SiCl4 (2 mol%) was added at 0 C, and the mixture was warmed to 60 C and stirred for 14 h until the disappearance of the starting amine as indicated by TLCor GC. When the reaction was complete, EtOAc (10 mL) and H2O (10 mL) was added, the organic phase was separated, and dried over Na2SO4. The solvent was removed under reduced pressure, and in most cases, pure product was obtained. If needed, the residue was purified by silica gel column chromatography (hexaneEtOAc). All materials had analytical data in good agreement with data in the literature.