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One pot synthesis of 4-hydroxy-3-substituted carbazoles via sulfoxide stabilised carbanion

โœ Scribed by Arasambattu I. Mohanakrishnan; Panayencheri C. Srinivasan

Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
178 KB
Volume
34
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A convenient method for the synthesis of 4-hydroxy-3-substitutedcarbazoles (Potential intermediate for pyridocarbazole alkaloids) from ethyl 5-methoxy-2-phenylsulfinylmethyl-l-phenylsulfonylindole-3-carboxylate is reported. Many annelation methods based on the Michael addition followed by intramolecular cyclisation have been reported'. However a similar approach to carbazoles from indole was unknown till recently. In continuation of our attempts to synthesize *c' ring oxygenated pyridocarbaeole alkaloids and also prompted by a recent report2 on the synthesis of dimethyll-aryl-4-hydroxy-N-methylcarbazole-2,3-dicarbo~lates, we report here a facile synthesis of 4-hydroxy-3-substituted carbazoles from the bidentate synthon 2 by a Michael addition promoted annelation strategy involving a sulfoxide stabilised carbanion at indole-2-position. Me0 i) PhSH/NaH.THF -, OEt ii)leq. MCPBA,CHC13

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