A REINVESTIGATION OF THE SYNTHESIS OF TRANS-(+ -4A,10A-HEXAHYDRO[1,4]BENZODIOXINO[2,3-C]PYRIDINE/

Authors
PROCOPIOU PA CHERRY PC DEAL MJ LAMONT RB
Citation
Pa. Procopiou et al., A REINVESTIGATION OF THE SYNTHESIS OF TRANS-(+ -4A,10A-HEXAHYDRO[1,4]BENZODIOXINO[2,3-C]PYRIDINE/, Journal of the Chemical Society. Perkin transactions. I, (13), 1994, pp. 1773-1777
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
13
Year of publication
1994
Pages
1773 - 1777
Database
ISI
SICI code
0300-922X(1994):13<1773:AROTSO>2.0.ZU;2-Z
Abstract
A reinvestigation of the reaction of threo-(+/-)-2,3-dibromopentane-1, 5-diol 5 with the disodium salt of catechol has shown that the product is (2,3-dihydro[1,4]benzodioxin-2-yl)propane-1,3-diol 20 and not tran s-(+/-)-3-(2-hydroxyethyl)-2-(hydroxymethyl) -2,3-dihydro[1,4]benzodio xin 12, as assumed previously. Consequently )-1,2,3,4,4a,10a-hexahydro [1,4]benzodioxino[2.3-c] pyridine 3 could not have been isolated earli er, and we now report its unambiguous synthesis via the epoxide 8 as w ell as the crystal structure of the diol 20.