Synthesis 2015; 47(09): 1269-1279
DOI: 10.1055/s-0034-1380287
paper
© Georg Thieme Verlag Stuttgart · New York

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

Alavala Gopi Krishna Reddy
Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram – 502 205, Medak District, Andhra Pradesh, India   Email: [email protected]
,
Gedu Satyanarayana*
Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram – 502 205, Medak District, Andhra Pradesh, India   Email: [email protected]
› Author Affiliations
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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