The regioselectivity of the formation of dihydro-and tetrahydrocarbazoles by the Fischer indole synthesis

…, PTW Cheng, S McLean

Index: Reed, G. W. Bryan; Cheng, Peter T. W.; McLean Stewart Canadian Journal of Chemistry, 1982 , vol. 60, p. 419 - 424

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Citation Number: 14

Abstract

The cyclohexanone 3 and the cyclohexenone 13 have been prepared, converted to their phenylhydrazones, and subjected to the Fischer indole synthesis under conditions ranging from 7% to 60% sulfuric acid in methanol. The tetrahydrocarbazoles 4 and 5 were isolated in a 2: 1 ratio in the sequence starting from 3 and no significant variation in the ratio was observed through the range of conditions used. In the sequence starting with 13, the ...