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2004
Carbazole derivatives
R 0150
Regioselective Synthesis of Mono- and Bis-decahydrobenzocarbazoles via Tandem Reactions of α-Diazo Ketones. — 1,3-Dipolar reactions of indole derivatives
49- 107 with
diazo ketones (II) afford oxa-bridged mono- and biscarbazole derivatives with
high regioselectivities. The presence of an electron-withdrawing substituent at the indole nitrogen, e.g. a benzoyl or phenylsulfonyl group, leads to decreased regioselectivities. In all cases, exo-isomers of oxa-bridged products are formed exclusively. In the
case of biscarbazoles (VII), this tandem intramolecular cyclization—intermolecular
cycloaddition sequence generates four carbon—carbon bonds, two carbon—oxygen
bonds and eight stereocenters to give highly functionalized products in a stereoselective
manner. — (MUTHUSAMY*, S.; GUNANATHAN, C.; SURESH, E.; Tetrahedron
60 (2004) 36, 7885-7897; Dep. Org. Chem., Cent. Salt Mar. Chem. Res. Inst.,
Bhavnagar 364 002, India; Eng.) — Klein
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