Efficient Brønsted acid-catalyzed aza-Michael reaction of amides and ureas with α,β-unsaturated enones under high-pressure conditions

Tetrahedron Letters

Volumn 50, Issue 1, 2009, Pages 48-50

  Azad, Saleha ^a   Kobayashi, Tomohiro ^a   Nakano, Keiji ^a   Ichikawa, Yoshiyasu ^a   Kotsuki, Hiyoshizo ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 ACETYL 1 CYCLOHEXENE; 2 CYCLOHEPTEN 1 ONE; 2 CYCLOHEXENONE; 2 CYCLOPENTEN 1 ONE; ALICYCLIC COMPOUND; AMIDE; BENZAMIDE; BRONSTED ACID; UNCLASSIFIED DRUG; UREA;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; MICHAEL ADDITION; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 56949092859     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.10.082     Document Type: Article

References (53)

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45. All new compounds gave satisfactory spectral data.
46. 2O was placed in a Teflon reaction vessel (1.5 mL volume), and the mixture was allowed to react at 0.6 GPa at 60 °C for a certain period of time to complete the reaction. After the reaction mixture was cooled and the pressure was released, the mixture was evaporated in vacuo. The crude product was purified by silica gel column chromatography (elution with hexane/EtOAc) to afford the pure adduct 3 or 5.
47. 3) δ 22.2, 30.8, 41.0, 47.6, 49.0, 126.9 (×2), 128.6 (×2), 131.7, 134.3, 166.8, 208.7.
48. 2O is unclear at present.
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50. 5CONHMe with 2a or 1a with 3-methyl-2-cyclohexen-1-one.
51. The same reaction under microwave irradiation (100 W, 150 psi, 100 °C, 35 min) produced 5a in only 20% isolated yield.
52. 3) δ 22.1, 31.0, 41.1, 48.1, 49.4, 120.6 (×2), 123.7, 129.3 (×2), 138.5, 155.1, 210.0.
53. Despite the extreme activity of the present method, however, no reaction was observed for 1a with methyl acrylate, methyl cinnamate, or acrylonitrile under the standardized conditions.