Abstract
Using trifluoroacetic acid as the condensing agent, the synthesis of novel 2-acetyl-1-hydroxycarbazoles has been achieved in moderate yield from 1-hydroxycarbazoles and acetyl chloride. Further, 2-acetyl-1-hydroxycarbazoles on base condensation with benzaldehyde followed by Prevost reaction with I2 – AgOAc in glacial AcOH yielded 2,3-dihydro-3-iodo-2-phenyl-4-oxopyrano[2,3-a]carbazoles which upon dehydroiodination afforded the biogenetically possible 2-phenyl-4-oxopyrano[2,3-a]carbazoles. Also, 2-acetyl-1-hydroxycarbazoles have been employed as synthones for the synthesis of annelated carbazoles viz. 3-methyl-pyrazolino- and 3-methyl-isoxazolo- [2,3-a]carbazoles.
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