Porphyrins with exocyclic rings. 1. Chemistry of 4, 5, 6, 7-tetrahydro-1H-indoles: synthesis of acetoxy derivatives, dihydroindoles, and novel porphyrins with four …

…, DL Zajeski, RP Balasubramaniam

Index: Lash, Timothy D.; Bladel, Karla A.; Shiner, Craig M.; Zajeski, Donna L.; Balasubramaniam, Rajiv P. Journal of Organic Chemistry, 1992 , vol. 57, # 18 p. 4809 - 4820

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Citation Number: 31

Abstract

A variety of 4, 5, 6, 7-tetrahydro-lH-indoles (THI's) and 4-0~ 0-4, 5, 6, 7-tetrahydro-lIf-indoles (4-oxoTHIs) have been synthesized from cyclohexanone and 1, 3-cyclohexanedione, respectively. The THI's reacted regioselectively with lead tetraacetate in acetic acid to give the 7-acetoxy derivatives. The isomeric CacetoxyTHI's were prepared by first reducing the corresponding 4-oxoTHI's with sodium borohydride and then reacting the resulting ...