Synthesis 2018; 50(17): 3540-3548
DOI: 10.1055/s-0036-1591591
paper
© Georg Thieme Verlag Stuttgart · New York

A Metal-Free Approach for the Synthesis of 2-Tetralones via Carbanion-Induced Ring Transformation of 2H-Pyran-2-ones

Samata E. Shetgaonkar
Chemistry Division, School of Advanced Science, VIT University, Chennai Campus, Chennai-600127, Tamil Nadu, India   Email: fatehveer.singh@vit.ac.in
,
Fateh V. Singh*
Chemistry Division, School of Advanced Science, VIT University, Chennai Campus, Chennai-600127, Tamil Nadu, India   Email: fatehveer.singh@vit.ac.in
› Author Affiliations
Further Information

Publication History

Received: 24 April 2018

Accepted after revision: 27 April 2018

Publication Date:
28 June 2018 (online)

Abstract

A metal-free, ultrasound-assisted approach for the synthesis of highly functionalized 2-tetralones in high yields is described. The process involves ring transformation of 2H-pyran-2-ones with the spirocyclic ketone 1,4-cyclohexandione monoethylene ketal to yield spiro­cyclic ketals and subsequent acid-mediated hydrolysis. This protocol is free from any organometallic reagents, is economical and tolerates a wide range of functional groups.

Supporting Information

 
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