Cross-Cycloaddition of Two Different Isocyanides: Chemoselective Heterodimerization and [3+2]-Cyclization of
Zhongyan Hu1, Haiyan Yuan1, Yang Men1
1Department of Chemistry, Northeast Normal University, Changchun, 130024, China.
Abstract:
A new cross-cycloaddition reaction between a wide range of isocyanides and 2-isocyanochalcones (or analogues) was developed for the expeditious synthesis of pyrrolo[3,4-b]indoles under thermal conditions. On the basis of the experimental results and DFT calculations, a mechanism for this domino reaction is proposed involving chemoselective heterodimerization of two different isocyanides to form 1,4-diazabutatriene intermediates, followed by an intramolecular [3+2]-cycloaddition and 1,3-proton shift.
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