Efficient Synthesis of Pseudoindoxyls from 2-Nitrobenzylidenemalonates and Indoles
Pallav Jyoti Arandhara1, Anil K Saikia1
1Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, Assam, India.
Abstract:
In this Letter, we have outlined a base-promoted highly efficient and mild synthetic route for constructing pseudoindoxyl derivatives, involving 2-nitrobenzylidenemalonates and indoles. This methodology enables the formation of a novel quaternary carbon center alongside a five-membered ring via Michael addition, followed by nucleophilic addition-elimination and a hydrolysis reaction in a cascade fashion. The reaction features a broad substrate scope, scalability, and excellent functional group tolerance with high yields. Additionally, postsynthetic modifications and photophysical studies demonstrate its versatility, making this elementary method a valuable tool for diverse synthetic applications involving pseudoindoxyl moieties.
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