D. Ram, B. Balram, D. Subhadra
Feb 1, 2001
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ChemInform
Abstract
In recent years 1-[3,4,5-trimethoxyphenyl]prop-2-eneI-one was used as an intermediate for the synthes is of 2,5-transdiaryltetrahydrofuran (potent PAF antagoni st). Some of the examples of PAF antagoni st prepared by thi s intermediate are CMI-392' , CMI206, MK-287 , L-652, 753, L-659, 989 etc. We report herein the synthesis and ant imic robia l act ivity of our title compound which is used as an intermedi ate for the synthes is of 2,5-transdiaryltetrahydrofuran . Condensation of our title compound with 3,4,5trimethoxybenzaldehyde followin g Biftu et al., proced ure gave 1,4-diketone. Reduction of diketone wi th NaBH4 in CH)OH (methanol) and tetrahydrofuran gave the 1,4-diol which was cyc li sed with orthophosphoric ac id in benzene at reflux temperature to give an equili brium mixture of cis and trans isomers of 2,5-transd iaryltetrahydrofuran. Synthes is of 2,5-transdiaryltetrahydrofuran is outlined in Scheme I. Compound 8 was obta ined in three steps from compound 4, following the procedure as previously descri bed. Compound 3 was prepared by alky lat ion of compound 2 with I ,2-d ibromoethane in 50% yield. Reaction of 3 with para-c hl orothiophenol gave 4 in 86.2% yield. Synthes is of 8 is out lined in Scheme II .