Synthesis of substituted 3,4-dihydroquinolin-2(1H)-one derivatives by sequential Ugi/acrylanilide [6π]-photocyclizations

Tetrahedron Letters

Volumn 48, Issue 20, 2007, Pages 3549-3552

  Akritopoulou Zanze, Irini ^a   Whitehead, Alan ^a   Waters, Jan E ^a   Henry, Rodger F ^a   Djuric, Stevan W ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDE; DIHYDROQUINOLINE DERIVATIVE;

ARTICLE; CHIRALITY; CIS TRANS ISOMERISM; CRYSTAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; UGI REACTION; X RAY CRYSTALLOGRAPHY;

EID: 34247177994     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.099     Document Type: Article

References (16)

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15. An immersion well reactor was employed following:. Penn J.H., and Orr R.D. J. Chem. Educ. 66 (1989) 86-88 When the reaction was performed in a capped vial placed next to a regular photochemical reactor, equipped with a quartz immersion well and a medium pressure, 450 W, mercury lamp, photocyclization was very sluggish and proceeded in poor yields
16. 2 was passed through the solution during the entire experiment. The solution was allowed to degass for 10 min and the mercury lamp was then turned on. The solution was irradiated for 2 h, concentrated and passed through a small plug of silica gel to yield a mixture of all diastereomers. The product mixture was further purified by column chromatography (15% EtOAc/hexanes) to give the pure major trans-diastereomer (31 mg, 48% yield).