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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References

1. Katritzky, A. R.; Rogers, J. W.; Witek, R. M.; Nair, S. K. Arkivoc 2004, viii, 52–60.         [ Links ]

2. Khan, B. U. J. Autism. Dev. Disord. 1997, 27, 479–489.         [ Links ]

3. Jeste, D. V.; Okamoto, A.; Napolitano, J.; Kane, J. M.; Martinez, R. A. Am. J. Psychiatry 2000, 157, 1150–1155.         [ Links ]

4. Kapui, Z.; Varga, M.; Urban–Szabo, K.; Mikus, E.; Szabo, T.; Szeredi, J.; Batori, S.; Finance, O.; Armani, P. J. Pharmacol. Exper. Therap. 2003, 305, 451–459.         [ Links ]

5. Awouters, F.; Vermeire, J.; Smeyers, F.; Vermote, P.; van Beek, R.; Niemegeers, C. J. E. Drug. Dev. Res. 1986, 8, 95–102.         [ Links ]

6. Motta, C. L.; Sartini, S.; Mugnaini, L.; Simorini, F.; Taliani, S.; Salerno, S.; Marini, A. M.; Settimo, F. D.; Lavecchia, A.; Novellino, E.; Cantore, M.; Failli, P.; Ciuffi, M. J. Med. Chem. 2007, 50, 4917–4927.         [ Links ]

7. Abass, M; Mayas, A. S. Heteroatom Chem. 2007, 18, 19–27.         [ Links ]

8. Abass, M.; Mostafa, B. B. Bioorg. Med. Chem. 2005, 13, 6133–6144.         [ Links ]

9. El–Shennawy, A. M.; Mohamed, A. H.; Abass, M. Med. Gen. Med. 2007, 9, 15–33.         [ Links ]

10. (a) Geies, A. A.; Bakhite, E. A.; El–Kashef, H. S. Pharmazie 1998, 53, 686–960;         [ Links ] (b) Zhang, L.–X.; Zhang, A.–J.; Chen, Z.–X.; Lei, X.–X.; Nan, X.–Y.; Chen, D.–Y.; Zhang, Z.–Y. Molecules 2002, 7, 681–689;         [ Links ] (c) Zhao, Z.; Leister, W. H.; Strauss, K. A.; Wisnoski, D. D.; Lindsley, C. W. Tetrahedron Lett. 2003, 44, 1123–1127.         [ Links ]

11. (a) Abass, M.; Othman, E. S. Synth. Commun. 2001, 31, 3361–3376;         [ Links ] (b) Lee, E.–J. J. Korean Chem. Soc. 2002, 46, 462–466.         [ Links ]

12. Ingalls, E. A.; Popp, F. D. J. Heterocycl. Chem. 1967, 4, 523–526.         [ Links ]

13. Tomita, K. J. Pharm. Soc. Japan (Yakugaku Zasshi) 1951, 71, 1100–1112.         [ Links ]

14. (a) Al–Soud, Y. A.; Al–Masoudi, N. A.; Loddo, R.; La Colla, P. Archiv. Pharm. 2008, 341, 365–369;         [ Links ] (b) Al–Soud, Y. A. Heteroatom Chem. 2007, 18, 443–448;         [ Links ] (c) Al–Soud, Y. A.; Al–Masoudi, N. A.; Ferwanah, A. E.–R. Bioorg. Med. Chem. 2003, 11, 1701–1708.         [ Links ]

15. Tominaga, Y.; Matsuoka, Y.; Oniyama, Y.; Uchimura, Y.; Komiya, H.; Hirayama, M.; Kohra, S.; Hosomi, A. J. Heterocycl. Chem. 1990, 27, 647–660.         [ Links ]