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RESEARCH ARTICLE
Contents Vol 72(7)

Versatile Synthesis of Functionalized Tetrahydroisoquinolines by Ring Transformation of 2H-Pyran-2-ones

Priyanka B. Kole A and Fateh V. Singh A B
+ Author Affiliations
- Author Affiliations

A Chemistry Division, School of Advanced Sciences, VIT Institute, Chennai Campus, Chennai-600127, Tamil Nadu, India.

B Corresponding author. Email: fatehveer.singh@vit.ac.in

Australian Journal of Chemistry 72(7) 524-532 https://doi.org/10.1071/CH19046
Submitted: 29 January 2019  Accepted: 4 April 2019   Published: 8 May 2019

Abstract

Functionalized tetrahydroisoquinolines are convenient precursors for the construction of numerous heterocyclic compounds of therapeutic importance. In this paper we have illustrated an efficient synthesis of highly substituted tetrahydroisoquinolines from 2H-pyran-2-ones via nucleophile-mediated ring transformation with tert-butyl-4-oxopiperidine-1-carboxylate followed by acid-mediated cleavage of the tert-butyloxycarbonyl group. The products were achieved smoothly in high yields with flexibility of various substituents.


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