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

Zakeyah Alsharif, Mohamad Akbar Ali, Hessa Alkhattabi, Derika Jones, Evan Delancey, P. C. Ravikumar, Mohammad A. Alam

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

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.

Original languageBritish English
Pages (from-to)14862-14870
Number of pages9
JournalNew Journal of Chemistry
Volume41
Issue number24
DOIs
StatePublished - 2017

Fingerprint

Dive into the research topics of 'Hexafluoroisopropanol mediated benign synthesis of 2: H -pyrido[1,2- a] pyrimidin-2-ones by using a domino protocol'. Together they form a unique fingerprint.

Cite this