Microwave induced one pot synthesis of dihydropyrimidine based on furochromone

International Journal of PharmTech Research

Volumn 1, Issue 3, 2009, Pages 857-862

  Abd El Rahman, N M ^a   Fawzy, N M ^a   Zaki, M E A ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Bignilli type reaction; Dihydropyrimidine; Microwave

Indexed keywords

5 ACETYL 4 (4,9 DIMETHOXY 5 OXO 5H FURO[3,2 G]CHROMEN 6 YL) 6 METHYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 6 (5 ACETYL 6 METHYL 2 THIOXO 1,2,3,4 TETRAHYDROPYRIMIDIN 4 YL) 4,9 DIMETHOXY 5H FURO[3,2 G]CHROMEN 5 ONE; DIHYDROPYRIMIDINE; ESTER DERIVATIVE; ETHYL 1,2,3,4 TETRAHYDRO 4 (4,9 DIMETHOXY 5 OXO 5H FURO[3,2 G]CHROMEN 6 YL) 6 METHYL 2 OXOPYRIMIDINE 5 CARBOXYLATE; ETHYL 1,2,3,4 TETRAHYDRO 4 (4,9 DIMETHOXY 5 OXO 5H FURO[3,2 G]CHROMEN 6 YL) 6 METHYL 2 THIOXOPYRIMIDINE 5 CARBOXYLATE; ETHYL 4 AMINO 1,2,5,6 TETRAHYDRO 6 (4,9 DIMETHOXY 5 OXO 5H FURO[3,2 G]CHROMEN 6 YL) 2 OXOPYRIMIDINE 5 CARBOXYLATE; ETHYL 4 AMINO 1,2,5,6 TETRAHYDRO 6 (4,9 DIMETHOXY 5 OXO 5H FURO[3,2 G]CHROMEN 6 YL) 2 THIOXOPYRIMIDINE 5 CARBOXYLATE; FUROCHROMONE DERIVATIVE; HETEROCYCLIC COMPOUND; HEXAHYDRO 4 (4,9 DIMETHOXY 5 OXO 5H FURO[3,2 G]CHROMEN 6 YL) 2,6 DIOXOPYRIMIDINE 5 CARBONITRILE; HEXAHYDRO 4 (4,9 DIMETHOXY 5 OXO 5H FURO[3,2 G]CHROMEN 6 YL) 6 OXO 2 THIOXOPYRIMIDINE 5 CARBONITRILE; PYRIMIDINE DERIVATIVE; TERT BUTYL 1,2,3,4 TETRAHYDRO 4 (4,9 DIMETHOXY 5 OXO 5H FURO[3,2 G]CHROMEN 6 YL) 6 METHYL 2 OXOPYRIMIDINE 5 CARBOXYLATE; TERT BUTYL 1,2,3,4 TETRAHYDRO 4 (4,9 DIMETHOXY 5 OXO 5H FURO[3,2 G]CHROMEN 6 YL) 6 METHYL 2 THIOXOPYRIMIDINE 5 CARBOXYLATE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MICROWAVE RADIATION; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION OPTIMIZATION; STRUCTURE ANALYSIS;

EID: 77951801067     PISSN: None     EISSN: 09744304     Source Type: Journal    
DOI: None     Document Type: Article

References (24)

1. Heravi M.M., Montazeri N. M., Rahimizadeh B.M, Ghassemzadeh M., J. of Chemical Res. 2004, 464.
2. Paul S. and Clark J. H,. Green Chemistry, 2003, 5, 635.
3. Clark J.H., Pure Appl Chem, 2001, 73, 103, Desai, b.B., Dallinger, D., Kappe C. O., Tetrahedron, 2006, 62, 4651.
4. Rovnyak G.C., Kimball S.D., Beyer B., Cucinotta G., DiMarco J.D., Gougoutas J., Hedberg A., Malley M., McCarthy J.P., Zhang R., Moreland S., J. Med. Chem., 1995, 38, 119.
5. Grover G.J., Dzwonczyk S., McMullen D.M., Normadinam C.S., Sleph P.G., Moreland S.J., "Pharmacologic profile of the dihydropyrimidine calcium channel blockers", SQ 32,547 and SQ 32,926 [correction of SQ 32,946]. J. Cardiovasc.Pharmacol.1995, 26, 289-294.
6. Sidler D.R., Larsen R.D., Chartrain M., Ikemoto N., Robrge C.M., Taylor C.S., Li,W., Bills G.F., PCT Int. Wo 99 07695.
7. Bruce M.A., Pointdexter G.S., Johnson G., PCT Int. Appl.WO 98 33, 791.
8. Jie Z., Mingjie Z., Bo L., Xiaojuan L., " New Ytterbium Complex-catalyzed Multicomponent Reactions for Synthesis of Dihydropyrimidines: [4+2] Cycloaddition vs. Biginelli Type Reaction", Chemistry Letters, 2009, 38(1), 56
9. Cox J. S. C., "Disodium cromoglycate", (Intal) Adv. Drug Res. 1970, 5, 115-96.
10. Bauer J., Selway J., Batchelor J., Tisdela M, Coell I.C. and Young D., Nature. 1981, 292, 369-.
11. Bailey D. M., "Annual Reports in Medicinal Chemistry". Academic Press Inc. 1981, 19,1212 .
12. Ishitsuka H, Ohsawa C., Umeda I. and Suhara Y., "Antipicornavirus flavone", Antimicrob. Agents Chemother.1982, 22, 611-616.
13. Biginelli P. G., Chim. Ital. 1893, 23,360.
14. Krenn W., Verdino P., Uray G., Faber K., Kappe C.O., "Determination of absolute configuration in 4-aryl-3,4-dihydro-2(1H)-pyrimidones by high performance liquid chromatography and CD spectroscopy", Chirality . 1999, 11, 659-662.
15. Fawzy N.M., Mandour A.H., and Zaki M.E.A., "Synthesis of New Furochromone-6-Pyrimidine and Pyrazoline Derivatives", Egypt. J. Chem. 2000, 43, 401-411.
16. Abd El-Rahman, N.M., "The behaviour of arylidenemalononitriles towards certain thiating phosphorus reagents". Heterocyclic Communications. 2002, 8, 465-468.
17. El-Kateb A.A., Abd El-Rahman N..M.., "Synthesis of New Heterocyclic Compounds Using Lawesson Reagent Phosphorus", Sulfur, and Silicon and the Related Elements, 2006, 181, 249-254.
18. Zaki M.E.A., Fernanda P. M., Booth B. L., "New and Efficient Synthesis of Imidazo[4,5-b]pyridine-5-ones" , Synlett.. 2005, 16, 2429.
19. Zaki M.E.A., Rashad A.E., Soliman H.A., Heikel O.A., " Pyrazolopyrano pyrimidines as a class of anti-inflammatory agents", Zeitschrift fur Naturforschung. 2006, 61C, 1-5.
20. Abdou I.M. and Strekowski L., "A Facile Synthesis of 6-Aryl-5-cyano-1-(β-D-pyranosyl or β-D-furanosyl)-2- thiocytosines", Tetrahedron, 2000, 56, 8631-8636.
21. Mithun A., Bantwal Sh., H., Nalilu S. K., "Convenient one pot synthesis of some novel derivatives of thiazolo[2,3-b]dihydropyrimidinone possessing 4-methylthiophenyl moiety and evaluation of their antibacterial and antifungal activities", European Journal of Medicinal Chemistry 2007, 42, 380 - 385.
22. Toma N. G., Heather T. and Kappe C.O., "Integration of high speed microwave chemistry and a statistical 'design of experiment' approach for the synthesis of the mitotic kinesin Eg5 inhibitor monastrol", Tetrahydron, 2008, 64, 2035-2041
23. Yadav J.S., Sabba B.A., "Microwave-assisted efficient synthesis of dihydro pyrimidines: improved high yielding protocol for the Biginelli reaction", J. Chem.Res., 2000, 354-355.
24. Kappe C.O., "A Reexamination of the Mechanism of the Biginelli Dihydro pyrimidine Synthesis. Support for an N-Acyliminium Ion Intermediate", J. Org. Chem.,1997, 62, 7201-7204.