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Novel syntheses of dihydroxanthyletin and dihydroseselin derivatives
Author(s) -
Jetter Michele M.,
Heindel Ned D.,
Laskin Jeffrey D.
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270433
Subject(s) - chemistry , ring (chemistry) , alkylation , coumarin , halide , closure (psychology) , carbon fibers , medicinal chemistry , stereochemistry , organic chemistry , catalysis , materials science , composite number , economics , market economy , composite material
Abstract In a one‐step alkylation, ring‐closure 7‐hydroxycoumarins are condensed in acid media with allyl and homoallyl halides or alcohols to linear 6,7‐dihydro‐2 H ,8 H‐ benzo[1,2–6:5,4‐ b' ]dipyran‐2‐ones. If both carbon‐6 and carbon‐8 are unsubstituted in the original coumarin, cyclization to angular isomers 9,10‐dihydro‐2 H ,8 H ‐benzo[1,2–6:3,4‐ b' ]dipyran‐2‐ones competes. These compounds are higher ring homologs of psoralens and angelicins commonly employed in phototherapy of skin disorders.