Superacid-Promoted Dual C–C Bond Formation by Friedel–Crafts Alkylation/Acylation of Cinnamate Esters: Synthesis of Indanones

Bokka Venkat Ramulu; Pedireddi Niharika; Gedu Satyanarayana

doi:10.1055/s-0034-1380385

Synthesis, Table of Contents

Synthesis 2015; 47(09): 1255-1268
DOI: 10.1055/s-0034-1380385

paper

Superacid-Promoted Dual C–C Bond Formation by Friedel–Crafts Alkylation/Acylation of Cinnamate Esters: Synthesis of Indanones

Bokka Venkat Ramulu

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

,

Pedireddi Niharika

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

Dual C–C bond formation was accomplished in one pot for the synthesis of a wide variety of indanones mediated by triflic acid. The reaction proceeds via an initial Michael-addition-type Friedel–Crafts alkylation followed by intramolecular acylation (cyclization). Significantly, the method was also successfully employed on more reactive β-diarylcinnamates using slightly different conditions.

Key words

cinnamates - Friedel–Crafts - indanones - alkylation - benzophenones

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References

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