Synthesis of 4-(3-hydroxyalkyl)pyrimidines by ring transformation reactions of 2-alkylidenetetrahydrofurans with amidines

Tetrahedron

Volumn 62, Issue 23, 2006, Pages 5426-5434

  Bellur, Esen ^a,b   Langer, Peter ^a,c  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b UNIVERSITY OF GREIFSWALD   (Germany)

^c LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Amidines; Heterocycles; Pyrimidines; Ring transformation; Tetrahydrofurans

Indexed keywords

1 (2,6 DIPHENYLPYRIMIDIN 4 YL)PENTAN 3 OL; 1 BROMO 4 (2,6 DIPHENYLPYRIMIDIN 4 YL)BUTAN 2 OL; 1 BROMO 4 (6 METHYL 2 PHENYLPYRIMIDIN 4 YL)BUTAN 2 OL; 1 CHLORO 4 (2,6 DIPHENYLPYRIMIDIN 4 YL)BUTAN 2 OL; 2 (2 METHYL 6 PHENYLPYRIMIDIN 4 YLMETHYL)BUTAN 1 OL; 2 (2,6 DIPHENYLPYRIMIDIN 4 YLMETHYL)BUTAN 1 OL; 2 METHYL 3 (2 METHYL 6 PHENYLPYRIMIDIN 4 YL)PROPAN 1 OL; 3 (2 DIMETHYLAMINO 6 PHENYLPYRIMIDIN 4 YL)PROPAN 1 OL; 3 (2 METHYL 6 PHENYLPYRIMIDIN 4 YL)PROPAN 1 OL; 3 (2,6 DIPHENYLPYRIMIDIN 4 YL) 2 METHYLPROPAN 1 OL; 3 (2,6 DIPHENYLPYRIMIDIN 4 YL)PROPAN 1 OL; 4 (2 METHYL 6 PHENYLPYRIMIDIN 4 YL)BUTAN 2 OL; 4 (2,6 DIPHENYLPYRIMIDIN 4 YL) BUTAN 2 OL; 4 (6 METHYL 2 PHENYLPYRIMIDIN 4 YL)BUTANE 1,2 DIOL; 5 (2 DIMETHYLAMINO 6 PHENYLPYRIMIDIN 4 YL)PENT 1 EN 3 OL; 5 (2 METHYL 6 PHENYLPYRIMIDIN 4 YL)PENT 1 EN 3 OL; 5 (2,6 DIPHENYLPYRIMIDIN 4 YL)PENT 1 EN 3 OL; AMIDINE; ETHER DERIVATIVE; FURAN DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; LITHIATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 33646202765     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.03.069     Document Type: Article

References (68)

1. Hassan N.A. Molecules 5 (2000) 827
2. references cited therein:
3. Pemmsin M., Lnu-Due C., Hoguet F., Gaultier C., and Narcisse J. Eur. J. Chem. 23 (1988) 543
4. Cannito A., Pemmsin M., Lnu-Due C., Hoguet F., Gaultier C., and Narcisse J. Eur. J. Chem. 25 (1990) 635
5. Smith P.A.S., and Kan R.O. J. Org. Chem. 29 (1964) 2261
6. Nega S., Aionso J., Diazj A., and Junquere F. J. Heterocycl. Chem. 27 (1990) 269
7. Tetsuo, S.; Mikio, T.; Hidetoshi, H.; Daijiro, H.; Akira, I. Jpn. Kokai Tokyo Koho JP 62,132,884, 1987;
8. Chem. Abstr. 107 (1987) 198350h
9. Chakaravorty, P. K.; Grelnlee, W. J.; Dooseap, K.; Mantlo, N. B.; Patchett, A. A. A.P.C.T. Int. Appl. WO 92.20.687.156, 1992
10. Chem. Abstr. 118 (1993) 213104d
11. Shishoo C.J., and Jain K.S. J. Heterocycl. Chem. 29 (1992) 883
12. Adlington R.M., Baldwin J.A., Catterick D., and Pritchard G.J. J. Chem. Soc., Perkin Trans. 1 (1999) 855
13. references cited therein:
14. Rosenthal G.A. Plant Nonprotein Amino and Imino Acids Biological, Biochemical and Toxicological Properties (1982), Academic, New York, NY p 117
15. Bell E.A. Biochim. Biophys. Acta 47 (1961) 602
16. Katritzky A.R., Soloducho J., and Belyakov S. ARKIVOC 1 (2000) 37
17. Spivey A.C., Srikaran R., Diaper C.M., and Turner D.J. Org. Biomol. Chem. 1 (2003) 1638
18. Bratušek U., Meden A., Svete J., and Stanovnik B. ARKIVOC V (2003) 77
19. Shutalev A.D., Kishko E.A., Sivova N.V., and Kuznetsov A.Y. Molecules 3 (1998) 100
20. Bowman M.D., Jeske R.C., and Blackwell H.E. Org. Lett. 6 (2004) 2019 and references cited therein
21. For cycloadditions, see:
22. Weichert A., and Hoffmann H.M.R. J. Org. Chem. 56 (1991) 4098
23. Tchelitcheff P. Bull. Soc. Chim. Fr. (1954) 672
24. Ireland R.E., and Haebich D. Chem. Ber. 114 (1981) 1418
25. Audrain H., Thorhauge J., Hazell R.G., and Joergensen K.A. J. Org. Chem. 65 (2000) 4487
26. for reactions with amines, see:
27. Detty M.R. J. Org. Chem. 44 (1979) 2073
28. Batra S., Srivastava S., Singh K., Chander R., Khanna A.K., and Bhaduri A.P. Bioorg. Med. Chem. 8 (2000) 2195
29. for cyclopropanations:
30. Kirmse W., and Rode K. Chem. Ber. 120 (1987) 847
31. for hydrogenations:
32. Ohta T., Miyake T., Seido N., Kumobayashi H., and Takaya H. J. Org. Chem. 60 (1995) 357 see also Ref. 2
33. Reviews:
34. Oivin T.L.B. Tetrahedron 43 (1987) 3309
35. Barrett A.G.M., and Sheth H.G. J. Org. Chem. 48 (1983) 5017
36. Rao Y.S. Chem. Rev. 76 (1976) 625
37. Pattenden G. Prog. Chem. Nat. Prod. 35 (1978) 133
38. Knight D.W. Contemp. Org. Synth. 1 (1994) 287
39. Gerlach H., and Wetter H. Helv. Chim. Acta 57 (1974) 2306
40. Schmidt U., Gombos J., Haslinger E., and Zak H. Chem. Ber. 109 (1976) 2628
41. Bartlett P.A., Meadows J.D., and Ottow E. J. Am. Chem. Soc. 106 (1984) 5304
42. Lygo B. Tetrahedron 44 (1988) 6889
43. Ley S.V., Lygo B., Organ H.M., and Wonnacott A. Tetrahedron 41 (1985) 3825
44. Booth P.M., Fox C.M.J., and Ley S.V. J. Chem. Soc., Perkin Trans. 1 (1987) 121
45. Mori K., Sasaki M., Tamada S., Suguro T., and Masuda S. Tetrahedron 35 (1979) 1601
46. For reviews of cyclization reactions of free and masked dianions, see:
47. Langer P. Chem.-Eur. J. 7 (2001) 3858
48. Langer P. Synthesis (2002) 441
49. Langer P., and Freiberg W. Chem. Rev. 104 (2004) 4125
50. Langer P., and Bellur E. J. Org. Chem. 68 (2003) 9742
51. see also:
52. Edwards G.L., and Sinclair D.J. Tetrahedron Lett. 40 (1999) 3933
53. Krueger S.A., and Bryson T.A. J. Org. Chem. 39 (1974) 3167
54. Gabriele B., Salerno G., De Pascali F., Costa M., and Chiusoli G.P. J. Organomet. Chem. 593-594 (2000) 409
55. Pflieger D., and Muckensturn B. Tetrahedron 45 (1989) 2031
56. Bellur E., and Langer P. Synlett (2004) 2169
57. Bellur E., and Langer P. Eur. J. Org. Chem. (2005) 4815
58. Bellur E., and Langer P. Synthesis 3 (2006) 480
59. Bellur E., and Langer P. Synlett (2004) 2172
60. Bellur E., and Langer P. J. Org. Chem. 70 (2005) 3819
61. Bellur E., and Langer P. J. Org. Chem. 70 (2005) 7686
62. Bellur E., Görls H., and Langer P. Eur. J. Org. Chem. (2005) 2074
63. Bellur E., Freifeld I., and Langer P. Tetrahedron Lett. 46 (2005) 2185
64. Bellur E., and Langer P. J. Org. Chem. 70 (2005) 10013
65. Detty M.R. J. Org. Chem. 44 (1979) 2073
66. Langer P., Holtz E., Karimé I., and Saleh N.N.R. J. Org. Chem. 66 (2001) 6057
67. Langer P., Armburst H., Eckardt T., and Magull J. Chem.-Eur. J. 8 (2002) 1443
68. Langer P., and Freifeld I. Chem.-Eur. J. 7 (2001) 565