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Journal of the Mexican Chemical Society

versión impresa ISSN 1870-249X

J. Mex. Chem. Soc vol.53 no.2 México abr./jun. 2009

 

Article

 

Substituted Pyridopyrimidinones. Part 3. Synthesis of Some Novel Ether Derivatives of 4H–Pyrido[1,2–a]pyrimidin–4–one

 

Mohamed Abass,* Mostafa M. Ismail, Wafaa R. Abdel–Monem, and Aisha S. Mayas

 

Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo 11757, Egypt. *Responsible author:mabass@chemist.com, quinolinone@yahoo.com

 

Received May 29, 2009
Accepted June 25, 2009

 

Abstract

A series of novel bis–heterocyclic ethers, containing 4H–pyrido[1,2–a]pyrimidin–4–one along with other five and six–membered heterocyclic rings, was obtained utilizing ethyl [(4–oxo–4H–pyrido[1,2–a]pyrimidin–2–yl)oxy]acetate (1), [(4–oxo–4H–pyrido[1,2–a]pyrimidin–2–yl)oxy]acetic acid (2) and/or [(4–oxo–4H–pyrido[1,2–a]pyrimidin–2–yl)oxy]acetohydrazide (3). Reaction of ester 1 with some ortho–hydroxy–aldehydes furnished the corresponding pyrido–pyrimidyloxypyrones. Reaction of ester 1 or acid 2 with 1,2–diamines led to some imidazoles. Also, some pyrazole, triazole, and oxadiazoline derivatives have been prepared from hydrazide 3.

Key words: Pyrido[1 ,2–a]pyrimidinone, Ethers, Pyrazoles, Oxadiazolines, Pyrones.

 

Resumen

Se preparó una serie de novedosos éteres bis–heterocíclicos que contienen el anillo de 4H–pirido[1,2–a]pirimidin–4–ona, unido con anillos heterocíclicos de seis miembros, empleando [(4–oxo–4H–pirido[1,2–a]pirimidin–2–il)oxi]acetato de etilo (1), ácido [(4–oxo–4H–pirido[1,2–a]pirimidin–2–il)oxi]acético (2) o [(4–oxo–4H–pirido[1,2–a]pirimidin–2–il)oxi]acetohidrazida (3). La reacción del éster 1 con algunos orto–hidroxi–aldehidos proporcionaron las piridopirimidiloxipironas correspondientes. La reacción del éster 1 o el ácido 2 con 1,2–diaminas condujeron a algunos imidazoles. Asimismo, se prepararon algunos derivados de pirazol, triazol y oxiadiazolina a partir de la hidrazina 3.

Palabras clave: Pirido[1,2–a]pirimidinona, éteres, pirazoles, oxadiazolinas, pirones.

 

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