Diversity oriented synthesis: Substitution at C5 in unreactive pyrimidines by Claisen rearrangement and reactivity in nucleophilic substitution at C2 and C4 in pteridines and pyrido[2,3-d]pyrimidines

Tetrahedron

Volumn 67, Issue 18, 2011, Pages 3226-3237

  Adcock, Jonathan ^a   Gibson, Colin L ^a   Huggan, Judith K ^a   Suckling, Colin J ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Antiparasitic activity; Claisen allyl rearrangement; Diversity oriented synthesis; Pteridines; Pyridopyrimidines; Pyrimidines

Indexed keywords

2 (BENZYLAMINO) 7 METHYL 6 [4 (TRIFLUOROMETHYL)BENZYL]PYRIDO[2,3 D]PYRIMIDIN 4(3H) ONE; 2 (BENZYLAMINO) 7 METHYL 6 [4 (TRIFLUOROMETHYL)BENZYL]PYRIDO[2,3 D]PYRIMIDINE 4(3H) ONE; 2 (BENZYLSULFANYL) 6 (METHYLAMINO) 4(H) PYRIMIDINONE; 2 (BENZYLSULFANYL) 6 CHLORO 4(3H) PYRIMIDINONE; 2 (BENZYLSULFANYL) 7 METHYL 6 [4 (TRIFLUOROMETHYL)BENZYL]PYRIDO[2,3 D]PYRIMIDIN 4(3H) ONE; 2 [(2,4 DIAMINO 1,6 DIHYDRO 6 OXOPYRIMIDIN 5 YL)METHYL] ACRYLIC ACID; 2 ANILINO 7 METHYL 6 [4 (TRIFLUOROMETHYL)BENZYL]PYRIDO[2,3 D]PYRIMIDIN 4(3H) ONE TRIFLUOROACETATE SALT; 3 [[[6 AMINO 2 (BENZYLSULFANYL) 4 PYRIMIDINYL]OXY]METHYL] 4 [4 (TRIFLUOROMETHYL)PHENYL] 3 BUTEN 2 ONE; 3 [[[6 AMINO 2 (BENZYLSULFANYL) 4 PYRIMIDINYL]OXY]METHYL] 4 PHENYL 3 BUTEN 2 ONE; 5 ALLYL 6 AMINO 2 (BENZYLTHIO) 4(3H) PYRIMIDINONE; 6 (ALLYLOXY) 2 (BENZYLSULFANYL) 4 PYRIMIDINYLAMINE; 6 (ALLYLOXY) 2 (BENZYLTHIO) PYRIMIDIN 4 AMINE 2 AND 3 ALLYL 6 AMINO 2 (BENZYLTHIO) PYRIMIDIN 4(3H) ONE; 6 AMINO 2 (BENZYLTHIO)PYRIMIDIN 4(3H) ONE; 6 BENZYL 2 (BENZYLSULFANYL) 7 METHYLPYRIDO[2,3 D]PYRIMIDIN 4(3H) ONE TRIFLUOROACETATE SALT; 7 METHYL 2 (1 PYRROLIDINYL) 6 [4 (TRIFLUOROMETHYL)BENZYL] PYRIDO[2,3 D]PYRIMIDIN 4(3H) ONE; 7 METHYL 6 [4 (TRIFLUOROMETHYL)BENZYL]PYRIDO[2,3 D]PYRIMIDINE 2,4(1H,3H) DIONE TRIFLUOROACETATE SALT; 8 ALLYL 2 (BENZYLSULFANYL) 6 METHYLPYRIDO[2,3 D]PYRIMIDINE 4,7(3H,8H) DIONE; 8 ALLYL 6 METHYL 2 (1 PYRROLIDINYL)PYRIDO[2,3 D]PYRIMIDINE 4,7(3H,8H) DIONE; CARBON; ESTER; ETHER DERIVATIVE; ETHYL 2 [(4 AMINO 2 (BENZYLSULFANYL) 1,6 DIHYDRO 6 OXOPYRIMIDIN 5 YL)METHYL] ACRYLATE; ETHYL 2 [[2 (BENZYLSULFANYL) 4 (METHYLAMINO) 6 OXO 1,6 DIHYDRO 5 PYRIMIDINYL]METHYL]ACRYLATE; ETHYL 2 [[4 (ALLYLAMINO) 2 (BENZYLSULFANYL) 6 OXO 1,6 DIHYDRO 5 PYRIMIDINYL METHYL] ACRYLATE; LEWIS ACID; PTERIDINE; PYRIMIDINE DERIVATIVE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; ASSAY; CATALYSIS; CHEMICAL BOND; CLAISEN REARRANGEMENT; CYCLIZATION; GRAM POSITIVE BACTERIUM; NOCARDIA; NONHUMAN; NUCLEOPHILICITY; PARASITE; PRIORITY JOURNAL; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS; TRYPANOSOMA BRUCEI;

NOCARDIA; POSIBACTERIA; TRYPANOSOMA BRUCEI BRUCEI;

EID: 79954421120     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.03.011     Document Type: Article

References (26)

1. C.L. Gibson, J.K. Huggan, and C.J. Suckling R.A. Jones, Comprehensive Heterocyclic Chemistry III 2008 Elsevier Oxford 915 975 Chapter 10.18
2. C.L. Gibson, S. La Rosa, K. Ohta, P.H. Boyle, F. Leurquin, A. Lemaon, and C.J. Suckling Tetrahedron 60 2004 943 959
3. Gibson, C. L.; Huggan, J. K.; Suckling, C. J.; Werner, E. R. Unpublished observations, 2006.
4. S.S. Al Hassan, R.J. Cameron, A.W.C. Curran, W.J.S. Lyall, S.H. Nicholson, D.R. Robinson, A. Stuart, I. Stirling, C.J. Suckling, and H.C.S. Wood J. Chem. Soc., Perkin Trans. 1 1985 1645 1659
5. J. Haddow, C.J. Suckling, and H.C.S. Wood J. Chem. Soc., Perkin Trans. 1 1989 1297 1304
6. C.L. Gibson, J.K. Huggan, A. Kennedy, L. Kiefer, J.-H. Lee, C.J. Suckling, C. Clements, A.L. Harvey, W.N. Hunter, and L.B. Tulloch Org. Biomol. Chem. 7 2009 1829 1842
7. C.J. Suckling, C.L. Gibson, J.K. Huggan, R.R. Morthala, B. Clarke, S. Kununthur, R.M. Wadsworth, S. Daff, and D. Papale Bioorg. Med. Chem. Lett. 18 2008 1552 1555
8. C.L. Gibson, S. La Rosa, and C.J. Suckling Org. Biomol. Chem. 1 2003 1909 1918
9. M. Melguizo, M. Nogueras, and A. Sanchez Heterocycles 32 1991 1719 1728
10. J. Negrillo, M. Nogueras, A. Sanchez, and A. Melgarejo Chem. Pharm. Bull. 36 1988 386 393
11. Huggan, J. K., Ph.D. Thesis, University of Strathclyde, 2006.
12. A.M.M. Castro Chem. Rev. 104 2004 2939 3002
13. C.J. Li Chem. Rev. 93 1993 2023 2035
14. H.J. Minnemeyer, J.A. Egger, J.F. Holland, and H. Tieckelmann J. Org. Chem. 26 1961 4425 4429
15. F.J. Dinan, H.J. Minkemeyer, and H. Tieckelmann J. Org. Chem. 28 1963 1015 1018
16. C.L. Gibson, J.K. Huggan, A.R. Kennedy, and C.J. Suckling Acta Crystallogr. E 2006 324 326
17. M. Shi, and Y.-S. Feng J. Org. Chem. 66 2001 406 411
18. A. Corma, and H. Garcia Chem. Rev. 103 2003 4307 4365
19. A.G. Jamieson, and A. Sutherland Org. Biomol. Chem. 5 2005 735 736
20. T.P. Yoon, V.M. Dong, and D.W.C. MacMillan J. Am. Chem. Soc. 121 1999 9726 9727
21. Z.-K. Wan, S. Wacharasindhu, E. Bunnun, and T. Mansour Org. Lett. 8 2006 2425 2428
22. D. Guiney, C.L. Gibson, and C.J. Suckling Org. Biomol. Chem. 1 2003 664 675
23. M. Menichincheri, M. Angiolini, D.F. Bassini, and M. Gude Tetrahedron Lett. 46 2005 8749 8752
24. S. Murata, K. Yoshikawa, and N. Chen Chem. - Eur. J. 11 2005 4835 4848
25. C.L. Gibson, J.K. Huggan, L. Kiefer, and C.J. Suckling G. Jansen, G.J. Peters, Chemistry and Biology of Pteridines and Folates 2007 SPS Publications Heilbronn 269 278
26. L.B. Tulloch, V.P. Martini, J. Iulek, J.K. Huggan, J.H. Lee, C.L. Gibson, T.K. Smith, C.J. Suckling, and W.N. Hunter J. Med. Chem. 53 2010 221 229