The Baylis-Hillman acetates as a valuable source for one-pot multistep synthesis: A facile synthesis of functionalized tri-/tetracyclic frameworks containing azocine moiety

Organic Letters

Volumn 9, Issue 13, 2007, Pages 2452-2456

  Basavaiah, Deevi ^a   Aravindu, Kunche ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547196801     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070380u     Document Type: Article

References (60)

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57. Detailed X-ray crystallographic data is available from the CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. for compounds 3 (CCDC no. 622201), 12 (CCDC no. 622202), 13 (CCDC no. 643665), and 15 (CCDC no. 622203).
58. 3 provided the trisubstituted alkene in 57% isolated yield as a mixture of E/Z isomers (E/Z = 78:22) [cyclicdiones provide very minor amounts of (Z)-isomer (<5%)]. Subsequent treatment of this trisubstituted alkene (containing E/Z isomers) with Fe/AcOH at reflux temperature did not provide the expected azocine moiety but resulted in the formation of 6-(2-aminophenyl)-5-methoxycarbonylhexan-2-one (reduced and mono deacetylated product) and the corresponding pure (E)-isomer was obtained after crystallization.
59. These reactions were carried out in DMF because in THF these were very sluggish probably because of solubility problems.
60. To examine whether the reaction was more facile and the yield of 15 would be higher using a stepwise method, we also isolated the trisubstituted alkene in 73% yield after the usual workup followed by column chromatography. Subsequent treatment of trisubstituted alkene with Fe/AcOH at reflux temperature for 1.5 h provided the desired tetracyclic azocine moiety 15 in 51% isolated yield (37% overall yield).