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

Samata E. Shetgaonkar; Fateh V. Singh

doi:10.1055/s-0036-1591591

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(17): 3540-3548
DOI: 10.1055/s-0036-1591591

paper

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

› Institutsangaben

Abstract

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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.

Key words

2-tetralones - 2H-pyran-2-ones - ring transformation reactions - 1,4-cyclohexanedione monoethylene ketal - spirocyclic ketals

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