Synthesis and biological evaluation of 4-fluoro-, 7-fluoro-, and 4, 7-difluoro-5, 6-dihydroxytryptamines

M Kawase, AK Sinhababu, EM McGhee…

Index: Kawase; Sinhababu; McGhee; Milby; Borchardt Journal of Medicinal Chemistry, 1990 , vol. 33, # 8 p. 2204 - 2211

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Citation Number: 7

Abstract

The 5, 6-dihydroxytryptamine (5, 6-DHT) derivatives 4-fluoro-and 7-fluoro-5, 6-DHTs (26a, b) and 4, 7-difluoro-5, 6-DHT (26c) were synthesized from 3-fluoroanisole (1) and 1, 4-difluoro- 2, 3-dimethoxybenzene (13), respectively. Efficient methods were developed for the conversion of 1 to 4-fluor@ and 7-fluoro-5, 6-bis (benzyloxy) indoles (12a, b, respectively) and 13 to 4, 7-difluoro-5, 6-[(diphenylmethy1ene) dioxylindole (19) via reductive ...