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Synthesis 2015; 47(09): 1269-1279
DOI: 10.1055/s-0034-1380287
DOI: 10.1055/s-0034-1380287
paper
A Facile, Superacid-Promoted Sequential Domino One-Pot Dual C–C Bond Formation and Fischer Indole Synthesis: Rapid Access to 10-Phenyl-5,10-dihydroindeno[1,2-b]indoles
Further Information
Publication History
Received: 02 January 2015
Accepted after revision: 10 February 2015
Publication Date:
12 March 2015 (online)
Abstract
A superacid-promoted sequential domino one-pot approach for the synthesis of novel 10-phenyl-5,10-dihydroindeno[1,2-b]indoles, ubiquitous core structure present in many alkaloid natural products, is presented. The entire sequential process involves a domino intermolecular Friedel–Crafts alkylation and intramolecular acylation of simple and easily accessible ethyl cinnamates, to furnish the corresponding indanones, followed by the Fischer indole reaction. Interestingly, this method enabled the synthesis of various dihydroindeno[1,2-b]indoles possessing tertiary or quaternary centers at the 10th position.
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