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

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 a...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2015-05, Vol.47 (9), p.1269-1279
Main Authors: Reddy, Alavala Gopi Krishna, Satyanarayana, Gedu
Format: Article
Language:English
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1380287