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Regioselective synthesis of [6c,12b-cis]-6c,7,12,13-tetrahydro-1H-chromeno[3=B4, 4=B4: 4,5]pyrano[2,3-c]chromen-1-onesvia unusual [1, 6] Michael addition

✍ Scribed by Krishna C. Majumdar; Pranab Chatterjee; Subrata Saha

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 116 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01528-7

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✦ Synopsis

Asyloxymethylpyrano[2,

[l]henzopyran-5(3H)-ones (la-f) on heating in N,N-diethylaniline snffereda [3s,3s] sigmatropic rearrangement followedby enolisation andan internal [1,61 Michael addition of the phenolic moiety to the diene-lactone moiety to give [6c,7,12b,4=B4 : 4,5]pyrano[2,3-c]chromen-l-ones (2a-f) in 65-75 % yield.

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