Biginelli-like reaction with dialkyl acetone-1,3-dicarboxylates: a remarkable case of steric control

Tetrahedron Letters

Volumn 49, Issue 21, 2008, Pages 3520-3523

  Světlík, Jan ^a   Veizerová, Lucia ^a   Kettmann, Viktor ^a  

^a Faculty of Natural Sciences   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CARBENE; CARBOXYLIC ACID DERIVATIVE; DIALKYL ACETONE 1,3 DICARBOXYLATE DERIVATIVE; ESTER DERIVATIVE; MONASTROL; PRODRUG; PYRIMIDINE DERIVATIVE; SALICYLALDEHYDE; TETRAHYDROPYRIMIDINE DERIVATIVE; THIOUREA; UREA;

ARTICLE; BIGINELLI REACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; CYCLIZATION; CYCLOADDITION; MICHAEL ADDITION;

EID: 42649143786     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.136     Document Type: Article

References (30)

1. Mayer T.U., Kapoor T.M., Haggarty S.J., King R.W., Schreiber S.J., and Mitchison T.J. Science 286 (1999) 971
2. Kapoor T.M., Mayer T.U., Coughlin M.L., and Mitchison T.J. J. Cell Biol. 150 (2000) 975
3. Wood K.W., Cornwell W.D., and Jackson J.R. Curr. Opin. Pharmacol. 1 (2001) 370
4. Wood K.W., and Bergnes G. Annu. Rep. Med. Chem. 39 (2004) 173
5. Sharp D.J., Rogers G.C., and Scholey J.M. Nature 407 (2000) 41
6. Endow S.A., and Baker D.S. Annu. Rev. Physiol. 65 (2003) 161
7. Sawin K.E., and Mitchison T.J. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 4289
8. Walczak C.E., Vernos I., Mitchison T.J., Karsenti E., and Heald R. Curr. Biol. 8 (1998) 903
9. Marcus A.I., Peters U., Thomas S.L., Garrett S., Zelnak A., Kapoor T.M., and Giannakakou P. J. Biol. Chem. 280 (2005) 11569
10. For reviews see:. Kappe C.O. Tetrahedron 49 (1993) 6937
11. Kappe C.O. Molecules 3 (1998) 1
12. Kappe C.O. Acc. Chem. Res. 33 (2000) 879
13. Kappe C.O. Eur. J. Med. Chem. 35 (2000) 1043
14. Kappe C.O., and Stadler A. Org. React. 63 (2004) 1
15. Svetlik J., Hanus V., and Bella J. J. Chem. Res. (S) (1991) 4
16. Kettmann V., and Svetlik J. Acta Crystallogr., Sect. C 52 (1996) 1496
17. Folkers K., Harwood H.J., and Johnson T.B. J. Am. Chem. Soc. 54 (1932) 3751
18. Lu J., Bai Y., Wang Z., Yang B., and Ma H. Tetrahedron Lett. 41 (2000) 9075
19. Lu J., and Bai Y. Synthesis (2002) 466
20. Tu S., Fang F., Zhu S., Li T., Zhang X., and Zhuang Q. Synlett (2004) 537
21. Rafiee E., and Jafari H. Bioorg. Med. Chem. Lett. 16 (2006) 2463
22. Fu N.Y., Yuan Y.F., Cao Z., Wang S.W., Wang J.T., and Peppe C. Tetrahedron 58 (2002) 4801
23. Kumar A., and Maurya R.A. Tetrahedron Lett. 48 (2007) 4569
24. Bose D.S., Sudharshan M., and Chavhan S.W. Arkivoc iii (2005) 228
25. 5 (304.31): C, 59.21; H, 5.30; N, 9.21. Found: C, 59.32; H, 5.33; N, 9.09. Product 4b: Mp 154-156 °C (EtOH), yield 36%; Product 4c: Mp 189-190 °C (EtOH), yield 48%; Product 4d: Mp 175-177 °C (MeOH), yield 35%; Product 4e: Mp 185-187 °C (MeOH); Product 4f: Mp 186-188 °C (MeOH), yield 44%.
26. Azizian J., Mohammadi A.A., Kohshari M., Karimi A.R., and Mohammadizadeh M.R. J. Heterocycl. Chem. 44 (2007) 455
27. +).
28. Bartashevich E.V., Plekanov P.V., Rusinov G.L., Potemkin V.A., Belik A.V., and Chupakhin O.N. Izv. Akad. Nauk SSSR, Ser. Khim. (1999) 1573
29. Crystallographic data (excluding structures factors) for the structures in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 679852 for 4a and 679853 for 5. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk.
30. Triggle D.J. In: McDonough S.I. (Ed). Calcium Channel Pharmacology (2004), Kluwer Academic/Plenum Publishers, Norwell 33-38 Chapter 3