Regioselective nitroso diels-alder cycloaddition reactions of 50-dienyl pyrimidinones and transformation to novel 4-amino-alcohol tethered pyrimidinones

Heterocycles

Volumn 77, Issue 1, 2009, Pages 547-556

  Anand, Amit ^b   Bhargava, Gaurav ^b   Singh, Pardeep ^b   Mahajan, Mohinder P ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

^b NONE

Author keywords

Amino Alcohol; Dihydrooxazine; Nitrosobenzene; Pyrimidinone; Zinc Glacial Acetic Acid

Indexed keywords

EID: 65549145780     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(F)76     Document Type: Article

References (44)

1. Botta M., Parlato M.C., Mugnaini C., Renzulli M.L., and Corelli F. Arkivoc 5 (2004) 349
2. Botta M., Occhionero F., Nicoletti R., Mastromarino P., Conti C., Margini M., and Saladino J. Bioorg. Med. Chem. 9 (1999) 1925
3. Boyd H.F., Fell S.C.M., Hickey D.M.B., Ife R.J., Leach C.A., Macphee C.H., Milliner K.J., Pinto I.L., Rawlings A., Smith S.A., Stansfield I.G., Stanway S.J., Theobald C.J., and Whittakerr C.M. Bioorg. Med. Chem. 12 (2002) 51
4. Hosni H.M., Basyouni W.M., and El-Nahas H.A. J. Chem. Res. (1999) 646
5. Tietze L.F., and Kettschau G. In: Metz P. (Ed). Topics in Current Chemistry (1997), Springer-Verlag, Berlin 189 and references therein
6. Boger D.L., and Weinreb S.M. In: Wasserman H.H. (Ed). Hetero Diels-Alder Methodology in Organic Synthesis (1987), Academic Press, San Diego, CA 47
7. Kirby G.W. Chem Soc. Rev. 6 (1977) 1
8. Kirby G.W., and Sweeny J.G. J. Chem. Soc., Perkin Trans. 7 (1981) 3250
9. Kirby G.W., McGuigan H., and Mcclean D. J. Chem. Soc., Perkin Trans. 1 (1985) 1961
10. Islam M.A., Kirby G.W., and Mahajan M.P. J. Chem. Soc,. Perkin Trans. 1 (1991) 1001
11. Gilchirst T. Chem. Soc. Rev. (1983)
12. Crystal E.J.T., Gilchrist T.L., and Stretch W. J. Chem. Res. 180 (1987) 1563 and references therein
13. Sharma A.K., Mazumdar S.N., and Mahajan M.P. Tetrahedron. Lett. 34 (1993) 7961
14. Vogt P.F., and Miller M.J. Tetrahedron 54 (1998) 1317
15. Sharma A.K., Mazumdar S.N., and Mahajan M.P. J. Chem. Soc. Perkin Trans. 1 (1997) 3065
16. Sharma A.K., Hundal G., Obrai S., and Mahajan M.P. J. Chem. Soc., Perkin Trans. 1 61 (1999) 15
17. Calvet G., Dussaussois M., Blanchard N., and Kouklovsky C. Org. Lett. 6 (2004) 2449
18. Calvet G., Guillot R., Blanchard N., and Kouklovsky C. Org. Biomol. Chem. 3 (2005) 4395
19. Marwaha A., Bhartam P.V., and Mahajan M.P. Tetrahedron. Lett. 46 (2005) 8253
20. Yamamoto H., and Momiyama N. Chem. Commun. (2005) 3514
21. Wichterle O. Collect. Czech. Chem. Commum. 12 (1947) 292
22. Sharma A.K., Jayakumar S., and Mahajan M.P. Tetrahedron Lett. 39 (1998) 7205
23. Sharma A.K., Jayakumar S., and Mahajan M.P. J. Chem. Soc., Perkin. Trans. 1 (2002) 774
24. Bhargava G., Kumar V., and Mahajan M.P. Tetrahedron Lett 48 (2007) 2365
25. A. I. Vogel, A. R. Tatchell, B. S. Furnis, A. J. Hannaford, and P. G. W. Smith, Vogels Text Book of Practical Organic Chemistry, 5, 956.
26. Momiyama N., Yamamoto Y., and Yamamoto H. J. Am. Chem. Soc. 129 (2007) 1190
27. Yamamoto Y., and Yamamoyo H. J. Am. Chem. Soc. 126 (2004) 4128
28. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), John Wiley & Sons, New York
29. Coppola G.M., and Schuster H.F. Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids (1987), Wiley, New York
30. Bergmeier S.C. Tetrahedron 56 (2000) 2561
31. Studer M., Blaser H.U., and Exner C. Adv. Synth. Catal 345 (2003) 345
32. Smaardijk A.A., and Wynberg H. J. Org. Chem. 52 (1987) 135
33. Wynberg H. In: Eliel E.L., and Wilen S. (Eds). Asymmetric Catalysis by Cinchona Alkaloids. In Topics in Stereochemistry (1986), Wiley-Interscience, New York 16
34. Muchow G., Vannoorenberghe Y., and Buono G. Tetrahedron Lett. 28 (1987) 6163
35. Chaloner P.A., and Langadianou E. Tetrahedron Lett. 28 (1987) 3013
36. Corey E.J., and Harmon F.J. Tetrahedron Lett. 28 (1987) 5237
37. Soai K., Yokoyama S., Ebihara K., and Hayasaka T. J. Chem. Soc., Chem. Commun. (1987) 1690
38. Soai K., Yokoyama S., and Hayasaka T. J. Org. Chem. 56 (1991) 4264
39. Lei A., Wu S., He M., and Zhang X. J. Am. Chem. Soc. 126 (2004) 1626
40. Zhong W.Y., Dong Z.Y., Fang K., Izumi K., Xu M.H., and Lin Q.G. J. Am. Chem. Soc. 127 (2005) 11956
41. Loh T.P., Huang J.M., Goh S.H., and Vittal J.J. Org. Lett. 2 (2000) 1291
42. Kedi G., and Truong A.P.. Org. Lett. 4 (2002) 3131
43. Leonard N.J., Playtis A.J., Skoog F., and Schmitz R.Y. J. Am. Chem. Soc. 93 (1971) 3056
44. J. Streith and A. Defoin, Synthesis, 1107.