Transformation of a N , N ‐Dimethylaniline N ‐Oxide into a Tetrahydroquinoline Scaffold via a Formal Polonovski‐Povarov Reaction

Author:

Isaac Elizabeth L.,Tumbelty Lauren N.,Chain* William J.

Abstract

Abstract Tetrahydroquinolines are among the most privileged scaffolds in organic chemistry. This chapter describes the procedure for transformation of a N,N‐dimethylaniline N‐oxide into a tetrahydroquinoline scaffold via a formal Polonovski‐Povarov reaction. It presents some of the important points to be considered, the conditions that need to be maintained, characterization data, and the reagents required, as well as the techniques used and the equipment setup that are vital to carrying out the process. The chapter also describes the hazards associated with working with chemicals and the ways to deal with these hazards.

Publisher

Wiley

Reference42 articles.

1. University of Delaware Department of Chemistry & Biochemistry 163 The Green Newark DE 19716. Financial support from the National Science Foundation (CHE‐1664954) and the University of Delaware are gratefully acknowledged. LNT gratefully acknowledges support by Award Number T32GM008550 from the National Institute of General Medical Sciences. The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institute of General Medical Sciences or the National Institutes of Health.

2. Safe and Convenient Procedure for Solvent Purification

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4. Asymmetric hydrogenation of aromatic compounds

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