THE SYNTHESIS OF 8A-METHOXY-2H,6H-CHROMEN-6-ONES AND CORRESPONDING 2H-CHROMENES BY A UNIQUE PROCESS UTILIZING PHENOLIC OXIDATION

Authors
PELTER A HUSSAIN A SMITH G WARD RS
Citation
A. Pelter et al., THE SYNTHESIS OF 8A-METHOXY-2H,6H-CHROMEN-6-ONES AND CORRESPONDING 2H-CHROMENES BY A UNIQUE PROCESS UTILIZING PHENOLIC OXIDATION, Tetrahedron, 53(11), 1997, pp. 3879-3916
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
11
Year of publication
1997
Pages
3879 - 3916
Database
ISI
SICI code
0040-4020(1997)53:11<3879:TSO8AC>2.0.ZU;2-3
Abstract
(Z)-1-Hydroxy-3-(3'-hydroxyphenyl)prop-2-enes undergo phenolic oxidati on by phenyliodonium diacetate (PIDA) in methanol to give 8a-methoxy-2 H,6H-dihydrochromen-6-ones. These are reduced by DIBAL-H to 2-substitu ted-Delta(3,4)-chromenes, the overall process being a unique heterocyc lic synthesis in which the heteroatom is not initially attached to a b enzene ring, but is introduced from a side chain. Parallel oxidations using is-1-hydroxy-3-(3'-hydroxyphenyl)prop-2,3-oxiranes have also bee n achieved despite the presence of the sensitive oxirane ring. (C) 199 7 Elsevier Science Ltd.