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; Gedu Satyanarayana

doi:10.1055/s-0034-1380287

Synthesis, Table of Contents

Synthesis 2015; 47(09): 1269-1279
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

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: gvsatya@iith.ac.in

,

Gedu Satyanarayana*

Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram – 502 205, Medak District, Andhra Pradesh, India Email: gvsatya@iith.ac.in

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Abstract

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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.

Key words

cinnamates - arenes - Friedel–Crafts reaction - Fischer indole synthesis - indoles - fused-ring systems

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References

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