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Conjugate Addition of Indoles to Nitroalkenes Promoted by Basic Alumina in Solventless Conditions
Author(s) -
Ballini Roberto,
Clemente Roberto Rabanedo,
Palmieri Alessandro,
Petrini Marino
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505339
Subject(s) - conjugate , chemistry , tandem , nitro , michael reaction , organic chemistry , combinatorial chemistry , cascade reaction , addition reaction , catalysis , nitroaldol reaction , nitromethane , enantioselective synthesis , mathematical analysis , alkyl , materials science , mathematics , composite material
Basic alumina is found to promote the conjugate addition of indoles to nitroalkenes in solventless conditions at 60 °C. Nitroalkenes can be replaced by nitro alcohols that are converted into nitroolefins under the reaction conditions. Alternatively, a tandem nitroaldol‐dehydration allows the utilization of nitroalkanes and aldehydes as remote precursors of reactive nitroalkenes in a ‘one–pot’ synthesis of 3‐substituted indoles.