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

Reddy, A G K and G, Satyanarayana (2015) 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. Synthesis, 47 (09). pp. 1269-1279. ISSN 0039-7881

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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.

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IITH Creators:
IITH CreatorsORCiD
G, SatyanarayanaUNSPECIFIED
Item Type: Article
Uncontrolled Keywords: arenes; cinnamates; Fischer indole synthesis; Friedel–Crafts reaction; fused-ring systems; indoles
Subjects: ?? sub5.8 ??
Divisions: Department of Chemistry
Depositing User: Team Library
Date Deposited: 23 Mar 2015 05:52
Last Modified: 24 Sep 2015 10:20
URI: http://raiithold.iith.ac.in/id/eprint/1414
Publisher URL: http://dx.doi.org/10.1055/s-0034-1380287
OA policy: http://www.sherpa.ac.uk/romeo/issn/0039-7881/
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