One-pot synthesis of pyrido[2,3-d]pyrimidines via efficient three-component reaction in aqueous media

A short and facile synthesis of pyrido[2,3-d]pyrimidine derivatives was accomplished in good yields via the three-component reaction of aldehydes, alkyl nitriles and aminopyrimidines in water in the presence of triethylbenzylammonium chloride (TEBAC). The structures of these compounds were characterized by elemental analysis, IR and 1H NMR spectra and further confirmed by single crystal X-ray diffraction analysis.

[1]  Q. Wang,et al.  New potential inhibitors of cyclin-dependent kinase 4: design and synthesis of pyrido[2,3-d]pyrimidine derivatives under microwave irradiation. , 2006, Bioorganic & medicinal chemistry letters.

[2]  D. Shi,et al.  One-pot Synthesis of N-Hydroxylacridine Derivatives in Water , 2005 .

[3]  D. Shi,et al.  Three‐Component One‐Pot Synthesis of 1,4‐Dihydropyrano[2,3‐c]pyrazole Derivatives in Aqueous Media , 2004 .

[4]  P. Bhuyan,et al.  A novel three-component one-pot synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines using microwave heating in the solid state , 2003 .

[5]  C. Kappe,et al.  High-throughput synthesis of N3-acylated dihydropyrimidines combining microwave-assisted synthesis and scavenging techniques. , 2003, Organic letters.

[6]  U. Bora,et al.  A novel microwave-mediated one-pot synthesis of indolizines via a three-component reaction. , 2003, Organic letters.

[7]  J. Iqbal,et al.  Cu(I)-catalyzed three component coupling protocol for the synthesis of quinoline derivatives , 2002 .

[8]  T. Arrhenius,et al.  A convenient solution and solid-phase synthesis of Δ5-2-oxopiperazines via N-acyliminium ions cyclization , 2002 .

[9]  Yu Yuan,et al.  Acid-free aza Diels-Alder reaction of Danishefsky's diene with imines. , 2002, Organic letters.

[10]  R. Olsson,et al.  A novel metal iodide promoted three-component synthesis of substituted pyrrolidines. , 2002, Organic letters.

[11]  M. N. Nasr,et al.  Pyrido [2, 3‐d]pyrimidines and Pyrimido[5′, 4′:5, 6]pyrido[2, 3‐d]pyrimidines as New Antiviral Agents: Synthesis and Biological Activity , 2002, Archiv der Pharmazie.

[12]  J. Bower,et al.  A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines. , 2002, Chemical communications.

[13]  Dennis H. Evans,et al.  One-step synthesis of substituted 6-amino-5-cyanospiro-4-(piperidine-4')- 2H,4H-dihydropyrazolo[3,4-b]pyrans. , 2002, Organic letters.

[14]  B. List,et al.  A Novel Proline‐Catalyzed Three‐Component Reaction of Ketones, Aldehydes, and Meldrum′s Acid. , 2001 .

[15]  S. Carloni,et al.  Clean synthesis in water. Part 2: Uncatalysed condensation reaction of Meldrum's acid and aldehydes , 2001 .

[16]  V. Nair,et al.  A novel synthesis of 2-aminopyrroles using a three-component reaction. , 2001, The Journal of organic chemistry.

[17]  S. Queener,et al.  Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase inhibitors and antitumor agents: synthesis and biological activities of 2,4-diamino-5-methyl-6-[(monosubstituted anilino)methyl] pyrido[2,3-d]pyrimidines. , 1999, Journal of medicinal chemistry.

[18]  F. Bigi,et al.  Montmorillonite KSF as an Inorganic, Water Stable, and Reusable Catalyst for the Knoevenagel Synthesis of Coumarin-3-carboxylic Acids. , 1999, The Journal of organic chemistry.

[19]  J. S. Sandhu,et al.  Studies on uracils: an efficient method for the synthesis of novel 1-allyl-6-(1′,2′,3′-triazolyl) analogues of HEPT , 1999 .

[20]  A. Doherty,et al.  Structure-activity relationships for a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors. , 1997, Journal of medicinal chemistry.

[21]  R. Ballini,et al.  CC bond fission via sulphones: A new ring cleavage of cyclic β-keto phenylsulphones , 1997 .

[22]  R. Ballini,et al.  The Michael reaction of nitroalkanes with conjugated enones in aqueous media , 1996 .

[23]  A. Vasudevan,et al.  2,4-diamino-5-deaza-6-substituted pyrido[2,3-d]pyrimidine antifolates as potent and selective nonclassical inhibitors of dihydrofolate reductases. , 1996, Journal of medicinal chemistry.

[24]  C. Monneret,et al.  Synthesis of deoxy analogs of HEPT involving a palladium (0) catalyzed coupling , 1994 .

[25]  Chao-Jun Li Organic reactions in aqueous media - with a focus on carbon-carbon bond formation , 1993 .

[26]  H. Mitsuya,et al.  Molecular targets for AIDS therapy. , 1990, Science.

[27]  J. S. Sandhu,et al.  Studies on uracils. 10. A facile one-pot synthesis of pyrido[2,3-d]- and pyrazolo[3,4-d]pyrimidines , 1990 .

[28]  J. S. Sandhu,et al.  Studies of pyrimidine-2,4-diones: synthesis of novel condensed pyrido[2,3-d]pyrimidines via intramolecular cycloadditions , 1988 .

[29]  J. S. Sandhu,et al.  Studies on Pyrimidine-Annelated Heterocycles; 8.1 Intramolecular Cycloaddition of Thiophene and Nitrile Oxide or Nitrone Groups Bonded to 1,3-Dimethyluracils , 1988 .

[30]  R. T. Walker,et al.  Synthesis and antiviral properties of (E)-5-(2-bromovinyl)-2'-deoxycytidine-related compounds. , 1988, Journal of medicinal chemistry.

[31]  E. De Clercq,et al.  Specific phosphorylation of 5-ethyl-2'-deoxyuridine by herpes simplex virus-infected cells and incorporation into viral DNA. , 1987, The Journal of biological chemistry.

[32]  E. De Clercq,et al.  2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity. , 1987, Journal of medicinal chemistry.

[33]  J Desmyter,et al.  Both 2',3'-dideoxythymidine and its 2',3'-unsaturated derivative (2',3'-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitro. , 1987, Biochemical and biophysical research communications.

[34]  E. Clercq Chemotherapeutic approaches to the treatment of the acquired immune deficiency syndrome (AIDS). , 1986 .

[35]  J. Burchenal,et al.  Synthesis and biological activities of 5-deaza analogues of aminopterin and folic acid. , 1986, Journal of Medicinal Chemistry.

[36]  E. Declercq Potential of bromovinyldeoxyuridine in anticancer chemotherapy. , 1986 .

[37]  Y. Kitade,et al.  Pyrimidines. 17. Novel pyrimidine to pyridine transformation reaction. One-step synthesis of pyrido[2,3-d]pyrimidines , 1981 .

[38]  R. Breslow,et al.  REVERSING THE SELECTIVITY OF CYCLODEXTRIN BISIMIDAZOLE RIBONUCLEASE MIMICS BY CHANGING THE CATALYST GEOMETRY , 1980 .

[39]  Tadashi. Sasaki,et al.  Search for a simpler synthetic model system for intramolecular 1,3-dipolar cycloaddition to the 5,6-double bond of a pyrimidine nucleoside , 1980 .

[40]  F. Yoneda,et al.  A NEW RING TRANSFORMATION OF ISOXAZOLO[3,4-d]PYRIMIDINES INTO PYRIMIDO[4,5-d]PYRIMIDINES , 1979 .

[41]  R. T. Walker,et al.  The synthesis of the potent anti-herpes virus agent, E-5(2-bromovinyl)-2′-deoxyuridine and related compounds , 1979 .

[42]  丸本 龍二,et al.  Kondensierte Pyrimidine. III. Synthese von Isoxazolo [3,4-d] pyrimidinen , 1977 .

[43]  T. Bradshaw,et al.  5-Substituted pyrimidine nucleosides and nucleotides , 1977 .

[44]  G. Anderson,et al.  Pyrido(2,3-d)pyrimidines. IV. Synthetic studies leading to various oxopyrido(2,3-d)pyrimidines. , 1976, The Journal of organic chemistry.

[45]  A. D. Broom,et al.  Studies on the acylation of some 6-aminouracil derivatives. , 1972, The Journal of organic chemistry.

[46]  A. Strecker Ueber die künstliche Bildung der Milchsäure und einen neuen, dem Glycocoll homologen Körper; , 1850 .