Hetero Diels-Alder reaction: A novel strategy to regioselective synthesis of pyrimido[4,5-d]pyrimidine analogues from Biginelli derivative

Tetrahedron

Volumn 61, Issue 17, 2005, Pages 4237-4248

  Sharma, Pratibha ^a   Kumar, Ashok ^a   Rane, Nilesh ^a   Gurram, Vamsi ^a  

^a DEVI AHILYA UNIVERSITY   (India)

Author keywords

Biginelli compound; Dienophile; Hetero Diels Alder cycloadditions; PM3; Pyrimido 4,5 d pyrimidines; Semiempirical

Indexed keywords

6 METHYL 4 PHENYL 2 THIOXO 1,2,3,4 TETRAHYDROPYRIMIDINE 5 CARBOXYLIC ACID; ALKADIENE; AMIDINE; CARBOXYLIC ACID DERIVATIVE; GUANIDINE DERIVATIVE; N ARYLIDINE GUANIDINE; N ARYLIDINE N' METHYLFORMAMIDINE; PYRIMIDINE DERIVATIVE; PYRIMIDO[4,5 D]PYRIMIDINE; UNCLASSIFIED DRUG;

ARTICLE; BIGINELLI REACTION; CALCULATION; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; EMPIRICISM; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR MECHANICS; NUCLEAR MAGNETIC RESONANCE; PREDICTION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS; THEORY;

BETULACEAE;

EID: 16244418702     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.066     Document Type: Article

References (30)

1. D.L. Boger, and S.M. Weinreb Hetero Diels-Alder Methodology in Organic Synthesis 1987 Academic San Diego
2. J.W. Daly, and T.F. Spande S.W. Pelletier Alkaloids: Chemical and Biological Perspectives Vol. 4 1986 Wiley New York 1 254
3. N.J. Curtin, H.C. Barlow, K.J. Bowman, A.H. Calvert, R. Richard Davison, B.T. Golding, B. Huang, P.J. Loughlin, D.R. Newell, P.G. Smith, and R.J. Griffin J. Med. Chem. 47 2004 4905 4922
4. J.P. De la Cruz, T. Carrasco, G. Ortega, and F. Sanchez de la Cuesta Lipid 27 1992 192 194
5. Y.S. Sanghvi, S.B. Larson, S.S. Matsumoto, L.D. Nord, D.F. Smee, R.C. Willis, T.H. Avery, R.K. Robins, and G.R. Revankar J. Med. Chem. 32 1989 629 637
6. G.W. Rewcastle, A.J. Bridges, D.W. Fry, J.R. Rubin, and W.A. Denny J. Med. Chem. 40 1997 1820 1826
7. D.W. Fry, M.A. Becker, and R.L. Switzer Mol. Pharma. 47 1995 810 815
8. J.E. Gready, C. McKinlay, and M.G. Gebauer Eur. J. Med. Chem. 38 2003 719 728
9. E.F. Reynolds Martindale The Extra Pharmacopoeia 28th ed. 1982 Pharmaceutical London p 1618
10. E.F. Reynolds Martindale The Extra Pharmacopoeia 28th ed. 1982 p 1730
11. P. Sharma, A. Kumar, S. Sharma, and N. Rane Bioorg. Med. Chem. Lett. 15 2005 937 943
12. P. Sharma, N. Rane, and V.K. Gurram Bioorg. Med. Chem. Lett. 14 2004 4185 4190
13. P. Sharma, S. Sharma, and N. Rane Bioorg. Med. Chem. 12 2004 3135 3139
14. P. Sharma, A. Kumar, and A. Mandloi Synthetic Commun. 33 2003 373 380
15. P. Sharma, A. Kumar, and P. Pandey Phosphorus Sulphur Silicon 178 2003 583 594
16. K. Hirota, Y. Kitade, M. Sajiki, and Y. Maki Synthesis 1984 589 590
17. K. Hirota, Y. Kitade, H. Sajiki, and Y. Maki J. Chem. Soc., Perkin Trans. 1 1990 123 128
18. S.W. Srivastava, W. Haq, and P.M.S. Chauhan Bioorg. Med. Chem. Lett. 9 1999 965 966
19. J.J.P. Stewart J. Comput. Chem. 10 1989 209 220
20. Stewart, J. J. P. MOPAC 6.0. QCPE 455; Indiana University: Bloomington, IN 47405, 1990.
21. J. Baker J. Comput. Chem. 7 1986 385 395
22. K. Fukui Acc. Chem. Res. 14 1981 363 368
23. C.O. Kappe, W.M.F. Fabian, and M.A. Semones Tetrahedron 53 1997 2803 2816
24. J.W. McIver Acc. Chem. Res. 7 1974 72 77
25. M.A. McCarrick, Y.D. Wu, and K.N. Houk J. Am. Chem. Soc. 114 1992 1499 1500
26. S.M. Bachrach, and L. Meixiao J. Org. Chem. 57 1992 6736 6744
27. K.N. Houk Acc. Chem. Res. 8 1975 361 369
28. P. Biginelli Gazz. Chim. Ital. 23 1893 360 416
29. For a review of the Biginelli reaction, see: C.O. Kappe Tetrahedron 49 1993 6937 6963
30. B.S. Furniss, A.J. Hannaford, P.W.G. Smith, and A.R. Tatchell Vogel's Text Book of Practical Organic Chemistry 5th ed. 1989 Addison Wesley Longman England