Synthesis of 1-substituted 2-azaspiro[4.5]deca-6,9-diene-8-ones and 2-azaspiro[4.5]deca-1,6,9-triene-8-ones by a three-component condensation of 1,2,3-, 1,2,4- or 1,3,5-trimethoxybenzene with isobutyric aldehyde and nitriles

Tetrahedron

Volumn 66, Issue 3, 2010, Pages 721-729

  Glushkov, Vladimir A ^a   Stryapunina, Olga G ^a   Gorbunov, Alexey A ^a   Maiorova, Olga A ^a   Slepukhin, Pavel A ^b   Ryabukhina, Sandra Ya ^c   Khorosheva, Elena V ^c   Sokol, Valentina I ^a   Shklyaev, Yurii V ^a  

^a INSTITUTE OF TECHNICAL CHEMISTRY   (Russian Federation)

^b INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

^c PERM STATE UNIVERSITY   (Russian Federation)

Author keywords

1,3,5 Trimethoxybenzene; 2 Azaspiro 4.5 deca 6,9 diene 8 ones; Nitriles; Three component condensation

Indexed keywords

2 AZASPIRO[4.5]DECA 1,6,9 TRIEN 8 ONE; 2 AZASPIRO[4.5]DECA 6,9 DIEN 8 ONE DERIVATIVE; ALKALOID DERIVATIVE; BENZENE DERIVATIVE; ISOBUTYRALDEHYDE; NITRILE; SULFURIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL;

EID: 71649108192     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.11.055     Document Type: Article

References (44)

1. Sandmeier P., and Tamm C. Helv. Chim. Acta 72 (1989) 784
2. Yang Y., Chang F., and Wu Y. Helv. Chim. Acta 87 (2004) 1392
3. Badger A.M., Schwartz D.A., Picker D.H., Dorman J.W., Bradley F.C., Cheeseman E.N., DiMartino M.J., Hanna N., and Mirabelli C.K. J. Med. Chem. 33 (1990) 2963
4. Kazmierski W.M., Furfine E., Spaltenstein A., and Wright L.L. Bioorg. Med. Chem. Lett. 12 (2002) 3431
5. Jolly R.S., and Livinghouse T. J. Am. Chem. Soc. 110 (1988) 7536
6. Clark A.J., Geden J.V., Thom S., and Wilson P. J. Org. Chem. 72 (2007) 5923
7. Cossy J., Bouzide A., and Leblanc C. J. Org. Chem. 65 (2000) 7257
8. Ibarra-Rivera T.R., Gámez-Montaño R., and Miranda L.D. Chem. Commun. (2007) 3485
9. Riston G.M., and Schwanz M.A. Tetrahedron Lett. 29 (1988) 2643
10. Ashimori A., Bachand B., Calter M.A., Gover S.P., Overman L.E., and Poon D. J. Am. Chem. Soc. 120 (1998) 6477
11. Aillaud I., Collin J., Duhayon C., Guillot R., Lyubov D., Shulz E., and Trifonov A. Chem.-Eur. J. 14 (2008) 2189
12. Pilling A.W., Böhmer J., and Dixon D.J. Chem. Commun. (2008) 832
13. Ovens C., Martin J.G., and Procter D.J. Org. Lett. 10 (2008) 1441
14. Trzoss M., and Brimble M. Synlett (2003) 2042
15. Tang B.-X., Tang D.-J., Tang S., Yu Q.-F., Zhang Y.-H., Liang Y., Zhong P., and Li J.-H. Org. Lett. 10 (2008) 1063
16. Santra S., and Andreana P.R. Org. Lett. 9 (2007) 5035
17. Pearson A.J., and Wang X. J. Am. Chem. Soc. 125 (2003) 638
18. Pearson A.J., Sun H., and Wang X. J. Org. Chem. 72 (2007) 2547
19. Knölker H.-J., Baum E., and Kosub M. Synlett (2004) 1769
20. Pigge F.C., and Fang S. Tetrahedron Lett. 42 (2001) 17
21. Pigge F.C., Coniglio J.J., and Fang S. Organometallics 21 (2002) 4505
22. Pigge F.C., Coniglio J.J., and Rath N.P. J. Org. Chem. 69 (2004) 1161
23. Pigge F.C., Coniglio J.J., and Rath N.P. Organometallics 24 (2005) 5424
24. Pigge F.C., Coniglio J.J., and Dalvi R. J. Am. Chem. Soc. 128 (2006) 3498
25. Pigge F.C., Dhanya R., and Hoefgen E.R. Angew. Chem., Int. Ed. 46 (2007) 2887
26. Harcourt D.N., Hussian F., Taylor N., and Nasir M. J. Chem. Soc., Perkin Trans. 1 (1986) 1329
27. Gavin J.P., and Waigh R.D. J. Chem. Soc., Perkin Trans. 1 (1990) 503
28. Doi S., Shirai N., and Sato Y. J. Chem. Soc., Perkin Trans. 1 (1997) 2217
29. Shklyaev Y.V., Glushkov V.A., El'tzov M.A., Gatilov Y.V., Bagryanskaya I.Y., and Tolstikov A.G. Mendeleev Commun. (2005) 125
30. Glushkov V.A., Shklyaev Y.V., Sokol V.I., Sergienko V.S., and Davydov V.V. Mendeleev Commun. (1998) 227
31. Ausheva O.G., Glushkov V.A., Shurov S.N., and Shklyaev Y.V. Russ. Chem. Bull. 51 (2002) 894
32. Glushkov V.A., Anikina L.V., Vikharev Y.B., Stryapunina O.G., Shklyaev Y.V., and Tolstikov A.G. Pharmaceut. Chem. J. 38 (2004) 86
33. Nifontov Y.V., Glushkov V.A., Ausheva O.G., and Shklyaev Y.V. Russ. J. Org. Chem. 38 (2002) 1386
34. Nifontov Y.V., Glushkov V.A., and Shklyaev Y.V. Russ. Chem. Bull. 52 (2003) 437
35. Glushkov V.A., Vetoshkina T.N., Kolgashev D.V., Maiorova O.A., Shurov S.N., and Shklyaev Y.V. Russ. J. Org. Chem. 42 (2006) 1131
36. Shklyaev Y.V., Yeltsov M.A., Rozhkova Y.S., Tolstikov A.G., and Dembitsky V.M. Heteroat. Chem. 15 (2004) 486
37. Stryapunina O.G., Plekhanova I.V., Maiorova O.A., Glushkov V.A., and Shklyaev Y.V. Russ. J. Org. Chem. 44 (2008) 1752
38. Glushkov V.A., Shurov S.N., Maiorova O.A., Postanogova G.A., Feshina E.V., and Shklyaev Y.V. Chem. Heterocycl. Compd. 37 (2001) 444
39. Glushkov V.A., Ausheva O.G., Postanogova G.A., and Shklyaev Y.V. Chem. Heterocycl. Compd. (2000) 1344
40. Hey H.D., Leonard J.A., Moyneban T.M., and Rees C.W. J. Chem. Soc. (1961) 232
41. Wada M., Konishi H., Kirishima K., Takeuchi H., Natsume S., and Erabi T. Bull. Chem. Soc. Jpn. 70 (1997) 2737
42. Hoye T.R., and Kaese P.A. Synth. Commun. 12 (1982) 49
43. Sheldrick G.M. Program for the Solution of Crystal Structures. SHELXS -; 97 (1997), Univ. of Göttingen, Germany
44. Sheldrick G.M. Program for Refinement of Crystal Structure. SHELXL -; 97 (1997), Univ. of Göttingen, Germany