1429-22-7Relevant articles and documents
Synthesis of dihydrobenzo[h]coumarins and their 4-methyl analogs
Wang, Yang,Huang, Shaoxu,Xia, Peng
, p. 3141 - 3156 (2005)
Dihydrobenzo[h]coumarins (5a-7a) and their 4-methyl analogs (5b-7b) were synthesized from 1-naphthol via two different synthetic routes. One pathway is the direct condensation of 5,8-dihydro-1-naphthol (9) with malic acid or ethyl acetoacetate, affording 7,10-dihydrobenzo[h]coumarins 7a and 7b, respectively. The other is through the oxidation of 7,8,9,10-tetrahydrobenzo[h] coumarins (15a-b), followed by the reduction of the carbonyl group and dehydration of hydroxyl group, giving 7,8-dihydrobenzo[h]coumarins (5a, b) and 9,10-dihydrobenzo[h]coumarins (6a, b). The regio selectivities for the oxidation reactions of 15a, b were rationalized on the basis of quantum chemical calculations and further confirmed by the X-ray crystallographic analysis of the derivatives of oxidation products. Copyright Taylor & Francis, Inc.