Synlett 2017; 28(16): 2179-2183
DOI: 10.1055/s-0036-1590816
letter
© Georg Thieme Verlag Stuttgart · New York

Superacid-Mediated Intramolecular Cyclization/Condensation: Facile One-Pot Synthesis of Spirotetracyclic Indanones and ­Indenes

Bokka Venkat Ramulu
Indian Institute of Technology Hyderabad, Kandi-502 285, Sangareddy District, Telangana, India   eMail: gvsatya@iith.ac.in
,
Devarapalli Ravi Kumar
Indian Institute of Technology Hyderabad, Kandi-502 285, Sangareddy District, Telangana, India   eMail: gvsatya@iith.ac.in
,
Gedu Satyanarayana*
Indian Institute of Technology Hyderabad, Kandi-502 285, Sangareddy District, Telangana, India   eMail: gvsatya@iith.ac.in
› Institutsangaben

We are grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi, for financial support [No. 02(0262)/16/EMR-II].
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Publikationsverlauf

Received: 03. Mai 2017

Accepted after revision: 05. Juni 2017

Publikationsdatum:
11. Juli 2017 (online)


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Abstract

A facile, superacid-promoted, domino, one-pot synthesis of novel spirotetracyclic indanones through intramolecular Friedel–Crafts acylation/alkylation of α,β-unsaturated cinnamic acid esters is presented. Interestingly, when the β-aryl group contained electron-withdrawing substituents such as fluoro, chloro, or bromo, the reaction took a different mechanistic path and afforded arylindenes as the end products.

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