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Lewis Acid Mediated One‐Pot Synthesis of Aryl/Heteroaryl‐Fused Carbazoles Involving a Cascade Friedel–Crafts Alkylation/Electrocyclization/Aromatization Reaction Sequence
Author(s) -
Sureshbabu Radhakrishnan,
Saravanan Velu,
Dhayalan Vasudevan,
Mohanakrishnan Arasambattu K.
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.201001309
Subject(s) - aromatization , chemistry , friedel–crafts reaction , lewis acids and bases , cascade reaction , alkylation , aryl , toluene , organic chemistry , electrocyclic reaction , lewis acid catalysis , one pot synthesis , domino , brønsted–lowry acid–base theory , catalysis , medicinal chemistry , combinatorial chemistry , bicyclic molecule , alkyl
A Lewis‐acid‐mediated domino reaction of 2/3‐(bromomethyl)indoles with arenes/heteroarenes led to the formation of the corresponding annulated carbazoles. This three‐step one‐pot transformation proceeds by sequential Lewis acid catalysed Friedel–Crafts alkylation, electrocyclization and aromatization reactions. The strategy is highly efficient for the assembly of complex aryl/heteroaryl‐fused carbazoles.