Novel multicomponent reactions of primary amines and alkyl propiolates with alloxan derivatives in water

Tetrahedron

Volumn 64, Issue 45, 2008, Pages 10425-10430

  Teimouri, Mohammad Bagher ^a   Abbasi, Tayyebeh ^b   Mivehchi, Houri ^a  

^a IRAN POLYMER AND PETROCHEMICAL INSTITUTE   (Iran)

^b UNIVERSITY OF ZANJAN   (Iran)

Author keywords

Alkyl propiolate; Alloxan; Amine; Barbiturate; Multicomponent reaction

Indexed keywords

ALLOXAN; AMINE; BARBITURIC ACID DERIVATIVE; ETHYL 2 (5 HYDROXY 1,3 DIMETHYL 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 3 (ISOBUTYLAMINO) 2 PROPENOATE; ETHYL 2 (5 HYDROXY 2,4,6 TRIXOHEXAHYDRO 5 PYRIMIDINYL) 3 (ISOBUTYLAMINO) 2 PROPENOATE; ETHYL 3 (ADAMANTYLAMINO) 2 (5 HYDROXYL 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; ETHYL 3 (ALLYLAMINO) 2 (5 HYDROXYL 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; ETHYL 3 (BENZYLAMINO) 2 (5 HYDROXY 1,3 DIMETHYL 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; ETHYL 3 (HEXYLAMINO) 2 (5 HYDROXY 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; ETHYL 3 (PHENYLAMINO) 2 (5 HYDROXY 1,3 DIMETHYL 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; ETHYL 3 (PHENYLAMINO) 2 (5 HYDROXYL 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; ETHYL 3 (PROPYLAMINO) 2 (5 HYDROXY 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; METHYL 2 (5 HYDROXY 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDYL) 3 (ISOBUTYLAMINO) 2 PROPENOATE; METHYL 3 (4 HYDROXYANILINO) 2 (5 HYDROXYL 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; METHYL 3 (ALLYLAMINO) 2 (5 HYDROXYL 1,3 DIMETHYL 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; METHYL 3 (BENZYLAMINO) 2 (5 HYDROXY 1,3 DIMETHYL 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; METHYL 3 (BENZYLAMINO) 2 (5 HYDROXY 2,4,6 TRIOXOHEXHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; METHYL 3 (HEXYLAMINO) 2 (5 HYDROXY 1,3 DIMETHYL 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; METHYL 3 (HEXYLAMINO) 2 (5 HYDROXY 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; METHYL 3 (PHENYLAMINO) 2 (5 HYDROXYL 2,4,6 TRIOXOHEXAHYDRO 5 PYRIMIDINYL) 2 PROPENOATE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 52049094836     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.039     Document Type: Article

References (31)

1. Bojarski J.T., Mokrosz J.L., Barton H.J., and Paluchowska M.H. Adv. Heterocycl. Chem. 38 (1985) 229-297
2. In Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 9th ed.; Delgado, J. N., Remers, W. A., Lippincott, J. B., Eds.; Wolters Kluwer Health: Philadephia, PA, 1991.
3. Grams F., Brandstetter H., D'Alò S., Geppert D., Krell H.-W., Leinert H., Livi V., Menta E., Oliva A., and Zimmermann G. Biol. Chem. 382 (2001) 1277-1285
4. Foley L.H., Palermo R., Dunten P., and Wang P. Bioorg. Med. Chem. Lett. 11 (2001) 969-972
5. Lein M., Jung K., Ortel B., Stephan C., Rothaug W., Juchem R., Johannsen M., Deger S., Schnorr D., Loening S., and Krell H.-W. Oncogene 21 (2002) 2089-2096
6. Mangoldt D., Sinn B., Lein M., Krell H.W., Schnorr D., Loening S.A., and Jung K. Apoptosis 7 (2002) 217-220
7. Daniewski A.R., Liu W., and Okabe M. Org. Process Res. Dev. 8 (2004) 411-414
8. Mironov M.A. QSAR Comb. Sci. 25 (2006) 423-431
9. Dömling A. Chem. Rev. 106 (2006) 17-89
10. Ramón D.J., and Yus M. Angew. Chem., Int. Ed. 44 (2005) 1602-1634
11. Orru R.V.A., and de Greef M. Synthesis (2003) 1471-1499
12. Lancaster M. Green Chemistry: An Introductory Text (2002), Royal Society of Chemistry, Cambridge
13. Bezdek R.H., Wendling R.M., and DiPerna P. J. Environ. Manage. 86 (2008) 63-79
14. Dolle R.E., Bourdonnec B.L., Morales G.A., Moriarty K.J., and Salvino J.M. J. Comb. Chem. 8 (2006) 597-635
15. Ganesan A. Comb. Chem. 7 (2002) 47-55
16. Tietze L.F., and Modi A. Med. Res. Rev. 20 (2000) 304-322
17. Ugi I., and Heck S. Comb. Chem. High Throughput Screen. 4 (2001) 1-34
18. Zhu J., and Bienaymé H. Multicomponent Reactions (2005), Wiley-VCH, Weinheim
19. Teimouri M.B., and Khavasi H.R. Tetrahedron 63 (2007) 10269-10275
20. Teimouri M.B. Tetrahedron 62 (2006) 10849-10853
21. Teimouri M.B., and Bazhrang R. Bioorg. Med. Chem. Lett. 16 (2006) 3697-3701
22. Teimouri M.B., Shaabani A., and Bazhrang R. Tetrahedron 62 (2006) 1845-1848
23. Teimouri M.B., Bazhrang R., Eslamimanesh V., and Nouri A. Tetrahedron 62 (2006) 3016-3020
24. Sheldon R.G. Green Chem. 7 (2005) 267-278
25. Pirrung M.C. Chem.-Eur. J. 12 (2006) 1312-1317
26. Mironov M.A., Ivantsova M.N., Tokareva M.I., and Mokrushin V.S. Tetrahedron Lett. 46 (2005) 3957-3960
27. Pirrung M.C., and Sarma K.D. J. Am. Chem. Soc. 126 (2004) 444-445
28. Ribe S., and Wipf P. Chem. Commun. (2001) 299-307
29. Azizian J., Hatamjafari F., Karimi A.R., and Shaabanzadeh M. Synthesis (2006) 765-767
30. Rubin M.B., and Gleiter R. Chem. Rev. 100 (2000) 1121-1164
31. Schank K., Lieder R., Lick C., and Glock R. Helv. Chem. Acta 87 (2004) 869-924