Cascade assembly of N,N' -dialkylbarbituric acids and aldehydes: A simple and efficient one-pot approach to the substituted 1,5-dihydro-2H,2'H- spiro(furo[2,3-d]pyrimidine-6,5'-pyrimidine)-2,2',4,4',6'(1'H,3H,3'H)-pentone framework

Tetrahedron Letters

Volumn 51, Issue 50, 2010, Pages 6598-6601

  Elinson, Michail N ^a   Vereshchagin, Anatolii N ^a   Stepanov, Nikita O ^a   Belyakov, Pavel A ^a   Nikishin, Gennady I ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

2 3 Dihydrofuran formation; Aldehydes; Barbituric acids; Furo 2 3 d pyrimidine

Indexed keywords

1,1',3,3' TETRAETHYL 5 (4 METHYLPHENYL) 1,5 DIHYDRO 2H,2'H SPIRO(FURO[2,3 D]PYRIMIDINE 6,5' PYRIMIDINE) 2,2',4,4',6' (1'H,3H,3'H) PENTONE; 1,1',3,3' TETRAMETHYL 5 PHENYL 1,5 DIHYDRO 2H,2'H SPIRO(FURO[2,3 D]PYRIMIDINE 6,5' PYRIMIDINE) 2,2',4,4',6' (1'H,3H,3'H) PENTONE; 5 (2 CHLOROPHENYL) 1,1',3,3' TETRAMETHYL 1,5 DIHYDRO 2H,2'H SPIRO(FURO[2,3 D]PYRIMIDINE 6,5' PYRIMIDINE) 2,2',4,4',6' (1'H,3H,3'H) PENTONE; 5 (4 TERT BUTYLPHENYL) 1,1',3,3' TETRAMETHYL 1,5 DIHYDRO 2H,2'H SPIRO(FURO[2,3 D]PYRIMIDINE 6,5' PYRIMIDINE) 2,2',4,4',6' (1'H,3H,3'H) PENTONE; ALDEHYDE; BARBITURIC ACID; BROMINE; FURO[2,3 D]PYRIMIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; SPIRO(FURO[2,3 D]PYRIMIDINE 6,5' PYRIMIDINE)PENTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DRUG STRUCTURE; KNOEVENAGEL CONDENSATION; MICHAEL ADDITION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 78649394020     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.041     Document Type: Article

References (40)

1. Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324-337;
2. Nefzi, A; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449-472.
3. For reviews, see: (a) Tietze, L F. Chem. Rev. 1996, 96, 115-136;
4. Padwa, A. Pure Appl. Chem. 2003, 75, 47-62;
5. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134-7186.
6. Brunton, L. L.; Lazo, J. S.; Keith, L. P. Goodman & Gilman's the Pharmacological Basis of Therapeutics, 11th ed.; The McGraw-Hill Companies, Inc.: New York, 2006;
7. Johns, M. W. Drugs 1975, 9, 448-478;
8. Whittle, S. R.; Turner, A.J. Biochem. Pharmacol. 1982, 31, 2891-2895;
9. Chen, X.; Tanaka, K.; Yoneda, F. Chem. Pharm. Bull. 1990, 38, 307-311;
10. e) Naguib, F. N. M.; Levesque, D. L; Wang, E.-C.; Panzica, P. P.; El Kouni, M. H. Biochem. Pharmacol 1993, 46, 1273-1278;
11. (f) Bruner, H.; Ittnner, K. P.; Lunz, D.; Schmatloch, S.; Schmidt, T.; Zabel, M. Eur. J. Org. Chem. 2003, 855-862.
12. Lyons, K. E.; Pahwa, R. CNS Drugs 2008, 22, 1037-1045.
13. Sudha, S.; Lakshmana, M. K.; Pradhan, N. Pharmacol. Biochem. Behav. 1996, 54, 633-638.
14. (a) Grams, F.; Brandstetter, H.; D'Alo, S.; Gepperd, D.; Krel, H. W.; Leinert, H.; Livi, V.; Menta, E.; Oliva, A; Zimmermann, G. Biol Chem. 2001, 382, 1277-1285;
15. (b) Maquoi, E.; Sounni, N. E.; Devy, L.; Oliver, F.; Frankenne, F.; Krell, H. W.; Grams, F.; Foidart, J. M.; Noel, A. Clin. Cancer Res. 2004, 10, 4038-4047;
16. Uhlmann, C.; Froscher, W. CNS Neurosd Ther. 2009, 15, 24-31.
17. (a) Mokrosz, J. L. Pharmazie 1985, 40, 359-360;
18. (b) Prankerd, R. J.; McKeown, R. H. Int. J. Pharm. 1992, 83, 39-45;
19. Galati, E. M.; Monforte, M. T.; Miceli, N.; Raneri, E. Farmaco 2001, 56, 459-461;
20. Singh, P.; Paul, K.J. Heterocycl. Chem. 2006, 43, 607-612;
21. (e) Dundee, J. W.; Mcllroy, P. D. A. Anaesthesia 2007, 37, 726-734;
22. (f) Lomlin, L.; Einsiedel, J.; Heinemann, F. W.; Meyer, K.; Gmeiner, P. J. Org. Chem. 2008, 73, 3608-3611.
23. Elinson, M. N.; Feducovich, S. K.; Lizunova, T. L.; Nikishin, G. I. Elektrokhimiya 1996, 32, 42-52.
24. (a) Nikishin, G. I.; Elinson, M. N.; Feducovich, S. K. Izv. Akad. Nauk Ser. Khim. 1986, 1919-1920;
25. (b) Elinson, M. N.; Lizunova, T. L; Dekaprilevich, M. O.; Struchkov, Y. T.; Nikishin, G. I. Mendeleev Commun. 1993, 192-193;
26. Feducovich, S. K.; Elinson, M. N.; Nikishin, G. I. Izv. Akad. Nauk Ser. Khim. 1994, 1835-1836.
27. (a) Elinson, M. N.; Feducovich, S. K.; Zakharenkov, A. A.; Bushuev, S. G.; Pashchenko, D. V.; Nikishin, G. I. Mendeleev Commun. 1998, 15-17;
28. (b) Elinson, M. N.; Feducovich, S. K.; Starikova, Z. A.; Olessova, O. S.; Vereshchagin, A. N.; Nikishin, G. I. Tetrahedron Lett. 2000, 41, 4937-4941;
29. Elinson, M. N.; Feducovich, S. K.; Starikova, Z. A.; Vereshchagin, A. N.; Nikishin, G. I. Tetrahedron Lett. 2005, 46, 6389-6393;
30. Elinson, M. N.; Feducovich, S. K.; Starikova, Z. A; Vereshchagin, A N.; Belyakov, P. A; Nikishin, G. I. Tetrahedron 2006, 62, 3989-3996.
31. (a) Elinson, M. N.; Feducovich, S. K.; Uzunova, T. L.; Nikishin, G. I, Tetrahedron 2000, 56, 3063-3069;
32. (b) Elinson, M. N.; Feducovich, S. K.; Zaimovskaya, T. A.; Vereshchagin, A. N.; Nikishin, G. I. Izv. Akad. Nauk Ser. Khim. 2005,663-667;
33. Vereshchagin, A. N.; Elinson, M. N.; Zaimovskaya, T. A.; Nikishin, G. I. Tetrahedron 2008, 64, 9766-9770.
34. Elinson, M. N.; Vereshchagin, A. N.; Stepanov, N. O.; Zaimovskaya, T. A; Merkulova, V. M.; Nikishin, G. I. Tetrahedron Lett. 2010, 51, 428-431.
35. Vereshchagin, A. N.; Elinson, M. N.; Stepanov, N. O.; Nikishin, G. I. Mendeleev Commun. 2009, 19, 324-325.
36. 3J(H,H) - 8.3 Hz, 2H, CH, Ar), 7.29
37. Elinson, M. N.; Feducovich, S. K.; Stepanov, N. O.; Vereshchagin, A. N.; Nikishin, G. I. Tetrahedron 2008, 64, 708-713.
38. Elinson, M. N.; Vereshchagin, A N.; Stepanov, N. O.; Ilovaisky, A. I.; Vorontsov, A. Y.; Nikishin, G. I. Tetrahedron 2009, 65, 6057-6062.
39. Ded, M. L; Bhuyan, P.J. Tetrahedron Lett. 2005, 46, 6453-6466.
40. 'Towards the ideal synthesis': Wender, P. A.; Handy, S. T.; Wright, D. L. Chem, Ind. 1997, 765-769.