Synthesis of 5H-furo[3′,2′ : 6,7][1]benzopyrano[3,4-c]pyridin-5-ones and 8H-pyrano[3′,2′ : 5,6]benzofuro[3,2-c]pyridin-8-ones (pyridopsoralens)
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 225-229
- https://doi.org/10.1039/p19830000225
Abstract
5H-Furo[3′,2′ : 6,7][1]benzopyrano[3,4-c]pyridin-5-ones (pyrido[3,4-c]psoralens)(3) have been obtained by the von Pechmann reaction starting from 6-hydroxy-2,3-dihydrobenzofuran acetates plus 1-benzyl-3-ethoxycarbonylpiperidin-4-one and subsequent dehydrogenation. The synthesis of their 8H-pyrano[3′,2′ : 5,6]benzofuro[3,2-c]pyridin-8-one isomers (14) and (17) was achieved by two ways using: (i) ring closure of 4-formyl-3-hydroxy-2-methylbenzofuro[3,2-c]pyridine, and (ii) cyclisation of piperidinone O-(4,7-dimethylcoumarin-7-yl) oxime derivatives and aromatization.This publication has 2 references indexed in Scilit:
- Photochemotherapy (PUVA) of psoriasis using 3-carbethoxypsoralen, a non-carcinogenic compound in miceBritish Journal of Dermatology, 1979
- Psoralen synthesis. Improvements in furano ring formation. Application to the synthesis of 4,5',8-trimethylpsoralenThe Journal of Organic Chemistry, 1979