Substituted pyridopyrimidinones. Part 5. Behavior of 2-hydroxy-4-oxo-4H-pyrido[1,2-α]pyrimidine-3-carbaldehyde in nucleophilic condensation reactions
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Mohamed Abass
,
Mostafa Ismail
Abstract
Reactivity of 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (I) towards N- and C-nucleophiles was described. A series of new enaminones II–III, Schiff’s base IV, and hydrazinomethylenediketones V–VIII and X were prepared in good yields. Cyclization of compounds X was achieved by an action of acetic acid to give pyrazolo[3,4-d]pyrido[1,2-a]pyrimidines XI. Base catalyzed Knoevenagel condensation of aldehyde I with some active methyl and methylene compounds led to a series of chalcone-like derivatives XII, XV, XVII, XX, XXIII, XXV, XXVII, XXIX, XXXI, XXXII, and XXXV, in fair yields. Cyclization of enones XII, XV, and XX with hydrazine gave novel heterocyclyl substituted pyrazoles XIII, XVII, and XXI, respectively. Pyrano[2,3-d]pyrido[1,2-a]pyrimidine-2,5-diones XXXIII, XXXIV, and XXXVI derivatives were obtained via cyclization of their respective enone derivatives.
[1] Abass, M. (2000). Chemistry of substituted quinolinones. Part II. Synthesis of novel 4-pyrazolylquinolinone derivatives. Synthetic Communications, 30, 2735–2757. DOI: 10.1080/00397910008086898. http://dx.doi.org/10.1080/0039791000808689810.1080/00397910008086898Search in Google Scholar
[2] Abass, M., & Ismail, M. M. (2000). Chemistry of substituted quinolinones I. Synthesis of novel triazinylmethylquinolinone derivatives. Chemical Papers, 54, 187–195. Search in Google Scholar
[3] Abass, M., & Othman, E. S. (2001). Chemistry of substituted quinolinones. III. Synthesis and reactions of some novel 3-pyrazolyl-2-quinolinones. Synthetic Communications, 31, 3361–3376. DOI: 10.1081/SCC-100106047. http://dx.doi.org/10.1081/SCC-10010604710.1081/SCC-100106047Search in Google Scholar
[4] Belicová, A., Seman, M., Milata, V., Ilavsky, D., & Ebringer, L. (1997). Biological activity of new aza analogues of quinolones. Folia Microbiologica, 42, 193–198. DOI: 10.1007/BF02818977. http://dx.doi.org/10.1007/BF0281897710.1007/BF02818977Search in Google Scholar PubMed
[5] Dominguez, J., Charris, J., Iarrusso, L., Lopez, S., Lobo, G., & Riggione, F. (1996). Synthesis of pyridopyrimidone derivatives and their activity against P. falciparum in vitro. Il Farmaco, 51, 781–784. Search in Google Scholar
[6] Ferrarini, P. L., Mori, C., Armani, G., & Rossi, L. (1995). Synthesis of some 4H-pyrido[1,2-a]pyrimidin-4-ones as antimicrobial agents. Il Farmaco, 50, 69–72. Search in Google Scholar
[7] Hermecz, I., & Mészáros, Z. (1988). Pyrido[1,2-a]pyrimidines; New chemical entities in medicinal chemistry. Medicinal Research Reviews, 8, 203–230. DOI: 10.1002/med.2610080204. http://dx.doi.org/10.1002/med.261008020410.1002/med.2610080204Search in Google Scholar PubMed
[8] Ibrahim, S. S., Abdel-Halim, A. M., Ismail, M. M., & Othman, E. S. (1994). Synthesis of some heterocyclic rings as substituents to quinolone moiety. Indian Journal of Heterocyclic Chemistry, 4, 125–130. Search in Google Scholar
[9] Ingalls, E. A., & Popp, F. D. (1967). The preparation, structure and reactions of some “malonyl-α-aminopyridines”. Journal of Heterocyclic Chemistry, 4, 523–526. DOI: 10.1002/jhet.5570040411. http://dx.doi.org/10.1002/jhet.557004041110.1002/jhet.5570040411Search in Google Scholar
[10] Ismail, M. M., Abdel-Halim, A., & Abass, M. (1997). Quinolones substituted by different moieties. Part 2. Reactions of 1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carbaldehyde with acyclic active methylene compounds. Journal of the Serbian Chemical Society, 62, 977–986. Search in Google Scholar
[11] Janssen, C. G. M., Knaeps, A. G., Kennis, L. E. J., & Vandenberk, J. (1990). Novel 3-piperidinyl-1,2-benzisoxazoles. European Patent Application No. EP0368388. Munich, Germany: Europen Patent Office. Search in Google Scholar
[12] Kappe, T., Aigner, R., Jöbstl, M., Hohengassner, P., & Stadlbauer, W. (1995). Reactions of 3-acyl-4-hydroxy-2(1H)-quinolones with nitrogen bases. Heterocyclic Communications, 1, 341–352. 10.1515/HC.1995.1.5-6.341Search in Google Scholar
[13] Kapui, Z., Varga, M., Urban-Szabó, K., Mikus, E., Szabó, T., Szeredi, J., Bátori, S., Finance, O., & Arányi, P. (2003). Biochemical and pharmacological characterization of 2-(9-(2-piperidinoethoxy)-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yloxymethyl)-4-(1-methylethyl)-6-methoxy-1,2-benzisothiazol -3(2H)-one-1,1-dioxide (SSR69071), a novel, orally active elastase inhibitor. Journal of Pharmacology and Experimental Therapeutics, 305, 451–459. DOI: 10.1124/jpet.102.044263. http://dx.doi.org/10.1124/jpet.102.04426310.1124/jpet.102.044263Search in Google Scholar PubMed
[14] Kepe, V., Kocevar, M., & Polanc, S. (1996). One-pot synthesis of some 2H-pyran-2-one derivatives. Journal of Heterocyclic Chemistry, 33, 1707–1710. DOI: 10.1002/jhet.5570330626. http://dx.doi.org/10.1002/jhet.557033062610.1002/jhet.5570330626Search in Google Scholar
[15] La Motta, C., Sartini, S., Mugnaini, L., Simorini, F., Taliani, S., Salerno, S., Marini, A. M., Da Settimo, F., Lavecchia, A., Novellino, E., Cantore, M., Failli, P., & Ciuffi, M. (2007). Pyrido[1,2-a]pyrimidin-4-one derivatives as a novel class of selective aldose reductase inhibitors exhibiting antioxidant activity. Journal of Medicinal Chemistry, 50, 4917–4927. DOI: 10.1021/jm070398a. http://dx.doi.org/10.1021/jm070398a10.1021/jm070398aSearch in Google Scholar PubMed
[16] Matsuishi, N., Amano, M., Nakagawa, Y., Kakehi, N., Kawashima, T., & Omura, S. (1987). Pyrido[1,2-a]pyrimidine derivatives. European Patent Application No. EP0242230. Munich, Germany: Europen Patent Office. Search in Google Scholar
[17] Matsutani, S., Mizushima, Y., & Doteuchi, M. (1987). 9-(Substituted thio)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives, their manufacture and use. European Patent Application No. EP0218423. Munich, Germany: Europen Patent Office. Search in Google Scholar
[18] O’Mahony, M. J., West, P. J., Lindell, S. D., & Macritchie, J. A. (1997). Fungicidal pyridopyrimidines. British Patent No. GB2307177. Newport, South Wales, UK: British Patent Office. Search in Google Scholar
[19] Zacharias, G., Wolfbeis, O. S., & Junek, H. (1974). Über Anilinomethylenverbindungen der Cyclohexandione. Monatshefte für Chemie, 105, 1283–1291. DOI: 10.1007/BF00909865. http://dx.doi.org/10.1007/BF0090986510.1007/BF00909865Search in Google Scholar
© 2009 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
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Articles in the same Issue
- Immobilization of urease in poly(1-vinyl imidazole)/poly(acrylic acid) network
- Anodic reactions of sulphate in molten salts
- Fuels obtained by thermal cracking of individual and mixed polymers
- Synthesis, structure, and solvent-extraction properties of tridentate oxime ligands and their cobalt(II), nickel(II), copper(II), zinc(II) complexes
- Properties of a poly(ethylene glycol)-block-poly(γ-benzyl l-glutamate)-graft-poly(ethylene glycol) copolymer membrane
- Influence of tungsten sources on the synthesis and properties of ammonium dioxothiotungstate
- A Raman spectroscopy study on differently deposited DLC layers in pulse arc system
- 1,7′-dimethyl-2′-propyl-1H,3′H-2,5′-bibenzo[d]imidazole as a corrosion inhibitor of mild steel in 1 M HCl
- The role of acidity profile in the nanotubular growth of polyaniline
- Direct sulfenylation of acetone with benzothiazolesulfenamides to benzothiazolylthio-substituted alkylaminopropene: synthesis and application
- Substituted pyridopyrimidinones. Part 5. Behavior of 2-hydroxy-4-oxo-4H-pyrido[1,2-α]pyrimidine-3-carbaldehyde in nucleophilic condensation reactions
- Lidocaine hydrochloride preparations with ionic and non-ionic polymers assessed at standard and increased skin surface temperatures
- Phase separation in non-ionic surfactant Triton X-100 solutions in the presence of phenol
- Phase formation in sodium dodecylsulfate solutions in the presence of salicylic acid for preconcentration purposes
- Numerical properties of equations involving high-order derivatives of pressure with respect to volume
- Synthesis and characterization of conducting copolymer of (N 1,N 3-bis(thiophene-3-ylmethylene)benzene-1,3-diamine-co-3,4-ethylenedioxythiophene)
- Intercalation of non-aromatic heterocyclic amines into layered zirconium glycine-N,N-dimethylphosphonate
- Kinetics of catalytic Meerwein-Ponndorf-Verley reduction of aldehydes and ketones using boron triethoxide
