Synthesis 2015; 47(09): 1255-1268
DOI: 10.1055/s-0034-1380385
paper
© Georg Thieme Verlag Stuttgart · New York

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: [email protected]
,
Pedireddi Niharika
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: 23 January 2015

Accepted after revision: 23 February 2015

Publication Date:
31 March 2015 (online)


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.

Supporting Information

 
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