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NH4BF4-Promoted Three-Component Formal [3 + 1 + 1 + 1] Cascade Cyclization for the Synthesis of 2-Arylcarbazoles
Zhiwei Lin1, Ruixin Kuang1, Xinhua Peng1
1School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China.
Abstract:
A straightforward approach for the synthesis of 2-arylcarbazoles via a three-component [3 + 1 + 1 + 1] cascade reaction has been developed, involving two Knoevenagel condensations between aldehydes and nitromethane, a cross Diels-Alder cycloaddition of 3-indolyl olefins with aryl olefins, and elimination of nitrous acid. This protocol offers advantages including metal-free catalysis, readily accessible materials, operational simplicity, and broad substrate tolerance. The synthetic utility of the 2-arylcarbazoles and the method was demonstrated respectively by four derivatizations and the synthesis of naturally occurring Tjipanazole I.
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