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Issue 24, 2017

Hexafluoroisopropanol mediated benign synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using a domino protocol

Author affiliations

Abstract

A domino strategy has been used for the synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones. Four sequential reactions: aza-Michael addition, water elimination, intramolecular acyl substitution, and [1,3]-H shift were observed in this domino protocol. Hexafluoroisopropanol is used as a promotor and recyclable solvent in this cascade process. The availability of inexpensive 2-aminopyridines and a wide variety of Michael acceptors such as commercially available acrylates and unactivated Baylis–Hillman adducts makes this methodology a huge reservoir of novel fused N-heterocycles as bioactive and potential therapeutic agents. The reaction mechanism has been proposed and rationalized by density functional theory calculations. Products are obtained in up to 95% yield.

Graphical abstract: Hexafluoroisopropanol mediated benign synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using a domino protocol

Supplementary files

Article information


Submitted
06 Sep 2017
Accepted
19 Oct 2017
First published
20 Oct 2017

New J. Chem., 2017,41, 14862-14870
Article type
Paper

Hexafluoroisopropanol mediated benign synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using a domino protocol

Z. Alsharif, M. A. Ali, H. Alkhattabi, D. Jones, E. Delancey, P. C. Ravikumar and M. A. Alam, New J. Chem., 2017, 41, 14862 DOI: 10.1039/C7NJ03376A

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