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One‐Pot Synthesis of Fused Benzo[ c ]carbazoles by Photochemical Intramolecular Annulation of 3‐Acyl‐2‐haloindoles with Tethered Styrenes
Author(s) -
Lu ShenCi,
Wei ShiChao,
Wang WeiXia,
Zhang Wei,
Tu ZhiFeng
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100876
Subject(s) - chemistry , annulation , aromatization , carbazole , intramolecular force , electrocyclic reaction , pyridine , photochemistry , photoinduced electron transfer , electron transfer , bicyclic molecule , medicinal chemistry , stereochemistry , organic chemistry , catalysis
An efficient procedure for the synthesis of fused benzo[ c ]carbazoles has been achieved in moderate to high yields by the one‐pot photochemical annulation of 3‐acyl‐2‐haloindoles with tethered styrenes by photoinduced electron‐transfer coupling, electrocyclic reactions, and deacylative aromatization in the presence of pyridine. Fused furo[2,3‐ c ]carbazoles were also synthesized under the same conditions. 5,6‐Dihydrobenzo[ c ]pyrrolo[1,2,3‐ lm ]carbazoles were oxidized by DDQ to afford aromatic benzo[ c ]pyrrolo[1,2,3‐ lm ]carbazole products in moderate to high yields.