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2005
Carbazole derivatives
R 0150
A New Preparative Route to Substituted Carbazoles by Benzannulation. — A
method for the synthesis of substituted carbazoles (X) is developed starting from
31- 127 novel
readily available o-iodoanilines (I). The key intermediates (VIII) are prepared by Sonogashira coupling of N-tosyl derivatives (III) with propargyl alcohol (IV) followed by
oxidation and subsequent Wittig reaction of the aldehyde (VI). The formation of both
the heterocyclic ring and the aromatic ring in carbazoles (X) is achieved by a regiospecific benzannulation of the acids (VIII) in Ac2O. — (SERRA*, S.; FUGANTI, C.;
Synlett 2005, 5, 809-812; Ist. Chim. Ric. Mol. Sez., Dep. Chim. Mater. Ing. Chim.
Politec., I-20133 Milano, Italy; Eng.) — R. Staver
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