Synthesis of novel electron-deficient chromone-fused dienes via phosphine catalyzed [4+2] annulation

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2265-2267

  Waldmann, Herbert ^a,b   Bruss, Hanna ^a,b   Dückert, Heiko ^a,b   Kumar, Kamal ^a  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Benzopyrones; Dienes; Lewis base catalysis; Rearrangements

Indexed keywords

ACETYLENE; ALKADIENE; CARBOXYLIC ACID; CHROMONE DERIVATIVE; ESTER; PHOSPHINE;

ANNULATION REACTION; ARTICLE; CATALYSIS; ELECTRON; REACTION ANALYSIS; SYNTHESIS;

EID: 79953174882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.151     Document Type: Article

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24. General procedure for the [4+2] annulation of ketoester 7 with acetylenecarboxylates: A solution of chromonylketoester 7 (1.0 equiv), acetylene carboxylate 4 (1.3 equiv) and triphenylphosphine (0.2 equiv) in toluene (1 ml/mmol) was stirred at 60 °C for 10-30 min. The reaction was monitored by TLC using DCM/methanol (100:1) as eluent. The reaction mixture was directly purified by column chromatography on silica gel with cyclohexane/ethyl acetate (CH/EA) as the eluent.
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33. 3 solution for longer time, the amount of the minor isomer increased.