A green approach to the synthesis of fused uracils: Pyrano[2,3-d] pyrimidines. On-water one-pot synthesis by domino Knoevenagel/Diels-Alder reactions

Synthesis

Volumn , Issue 23, 2010, Pages 4021-4032

  Paasz, Aleksandra ^a  

^a JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

Diels Alder reactions; drugs; green chemistry; pyrano 2,3 d pyrimidines; solvent effects

Indexed keywords

DIELS-ALDER REACTION; DRUGS; GREEN CHEMISTRY; PYRANO[2,3- D ]PYRIMIDINES; SOLVENT EFFECTS;

ALDEHYDES; CATALYSTS; CONDENSATION; CONTRAST MEDIA; CYCLOADDITION; DICHLOROMETHANE; ETHERS; HEATING; ORGANIC SOLVENTS; STYRENE; SYNTHESIS (CHEMICAL); TOLUENE;

SUSPENSIONS (FLUIDS);

5 (4 BROMOPHENYL) 7 ETHOXY 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 5 (4 CHLOROPHENYL) 7 ETHOXY 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 5 (4 CYANOPHENYL) 7 ETHOXY 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 5 (4 NITROPHENYL) 7 (2 OXOOXAZOLIDIN 3 YL) 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 7 (2 OXOOXAZOLIDIN 3 YL) 5 PHENYL 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 7 (4 METHOXYPHENYL) 5 (4 NITROPHENYL) 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 7 (4 METHOXYPHENYL) 5 PHENYL 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 7 ETHOXY 1,3,5 TRIMETHYL 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 2,4(3H)DIONE; 7 ETHOXY 5 (2 FURYL) 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 7 ETHOXY 5 (2 THIENYL) 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 7 ETHOXY 5 (4 METHOXYPHENYL) 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 7 ETHOXY 5 METHYL 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 7 ETHOXY 5 PHENYL 2 THIOXO 1,5,6,7 TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4(3H)ONE; 7' ETHOXY 1',3' DIMETHYLSPIRO[CYCLOPENTANE 1,5' (1',5',6',7' TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 2',4'(3'H)DIONE)]; 7' ETHOXY 2' THIOXOSPIRO[CYCLOPENTANE 1,5' (1',5',6',7' TETRAHYDRO 2H PYRANO[2,3 D]PYRIMIDIN 4'(3'H)ONE)]; ALDEHYDE; DICHLOROMETHANE; PYRANO[2,3 D]PYRIMIDINE DERIVATIVE; STYRENE; THIOBARBITURIC ACID; TOLUENE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ARTICLE; CATALYST; CONTROLLED STUDY; CYCLOADDITION; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; KNOEVENAGEL CONDENSATION; ONE POT SYNTHESIS; STEREOCHEMISTRY;

EID: 78650270213     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258292     Document Type: Article

References (42)

1. Rideout D S., Breslow R, J. Am. Chem. Soc. 1980 102 7816
2. Narayan S, Muldoon J M., Finn G V., Fokin V, Kolb H C., Sharpless K B., Angew. Chem. Int. Ed. 2005 44 3275
3. Jovanovic M V., Biel E R., J. Org. Chem. 1987 24 191
4. Haldar M K., Scott M D., Sule N, Srivastava D K., Mallik S, Bioorg. Med. Chem. Lett. 2008 18 2373
5. Kitamura N, Onishi A, EP 163599 1984; Chem. Abstr. 1984, 104, 186439
6. Furuja S, Ohtaki T, EP Application 608565 1994; Chem. Abstr. 1994, 121, 205395
7. Heber D, Heers C, Ravens U, Pharmazie 1993 48 537
8. Coates W, EP 351058 1990; Chem. Abstr. 1990, 113, 40711
9. Sakuma Y, Hasegawa M, Kataoka K, Hoshina K, Yamazaki N, Kadota T, Yamaguchi H, WO Application 9105785 1989; Chem. Abstr. 1989, 115, 71646
10. Anderson G L., Shim J L., Broom A D., J. Org. Chem. 1976 41 1095
11. Ahluvalia V K., Sharma H R., Tyagi R, Tetrahedron 1986 42 4045
12. Wamhoff H, Muhr J, Synthesis 1988 919
13. Ahluwalia V K., Kumar R, Khurana K, Batla R, Tetrahedron 1990 46 3953
14. Hirota K, Kuki H, Maki Y, Heterocycles 1994 37 563
15. Srivastava P, Saxena A S., Ram V J., Synthesis 2000 541
16. Devi I, Kumar B S. D., Bhuyan P J., Tetrahedron Lett. 2003 44 8307
17. Devi I, Bhuyan P J., Tetrahedron Lett. 2004 45 7727
18. Devi I, Borah H N., Bhuyan P J., Tetrahedron Lett. 2004 45 2405
19. Naya S, Miyagawa M, Nitta M, Tetrahedron 2005 61 4919
20. Brufola G, Fringuelli F, Piermatti O, Pizzo F, Heterocycles 1997 45 1715
21. Binev I G., Binev Y G., Stamboliyska B A., Juchnovski I N., J. Mol. Struct. 1997 435 235
22. Ayoubi S A., Texier-Boullet F, Hamelin J, Synthesis 1994 258
23. Jursic B S., Stevens E D., Tetrahedron Lett. 2003 44 2203
24. Deb M L., Bhuyan P J., Tetrahedron Lett. 2005 46 6453
25. Paasz A, Monatsh. Chem. 2008 139 1397
26. Bushweller C H., ONeil J W., Tetrahedron Lett. 1969 4713
27. Sankararaman S, Pericyclic Reactions - A Textbook Wiley-VCH Weinheim 2005
28. Tietze L F., Meier H, Nutt H, Chem. Ber. 1989 122 643
29. Tietze L F., Stegelmeier H, Harms K, Brumby T, Angew. Chem., Int. Ed. Engl. 1982 21 863
30. Tietze L F., Brumby T, Brand S, Bratz M, Chem. Ber. 1988 121 499
31. Tietze L F., Bachmann J, Wichmann J, Burkhardt O, Synthesis 1994 1185
32. Tietze L F., Brand S, Pfeiffer T, Antel J J., Harms K, Sheldrick G M., J. Am. Chem. Soc. 1987 109 921
33. Tietze L F., Chem. Rev. 1996 96 115
34. Tietze L F., Brasche G, Gericke K M., Domino Reactions in Organic Synthesis Wiley-VCH Weinheim 2006
35. Tietze L F., Kettschau G, Top. Curr. Chem. 1997 189 1
36. Bogdanowicz-Szwed K, Paasz A, Z. Naturforsch., B 2001 56 416
37. Paasz A, Org. Biomol. Chem. 2005 3 3207
38. Hu Y, Chen Z C., Le Z G., Zheng Q G., Synth. Commun. 2004 34 4521
39. Wang C, Ma J, Zhou X, Zang X, Wang Z, Gao Y, Cui P, Synth. Commun. 2005 35 2759
40. Medien H A. A., Zahran A A., Phosphorus, Sulfur Silicon Relat. Elem. 2003 178 1069
41. Shi D Q., Chen J, Zhuang Q Y., Wang X S., Hu H W., Chin. Chem. Lett. 2003 14 1242
42. Moskvin A V., Polkovnikova I I., Ivin B A., Russ. J. Gen. Chem. 1998 68 801