Switchable selectivity in multicomponent heterocyclizations of acetoacetamides, aldehydes, and 3-amino-1,2,4-triazoles/5-aminopyrazoles

Tetrahedron

Volumn 67, Issue 48, 2011, Pages 9389-9400

  Muravyova, Elena A ^a   Desenko, Sergey M ^a,b   Rudenko, Roman V ^a   Shishkina, Svetlana V ^a   Shishkin, Oleg V ^a,b   Sen'ko, Yulia V ^a   Vashchenko, Elena V ^a   Chebanov, Valentin A ^a  

^a INSTITUTE FOR SINGLE CRYSTALS   (Ukraine)

^b V N KARAZIN KHARKIV NATIONAL UNIVERSITY   (Ukraine)

Author keywords

Acetoacetamide; Aminoazole; Multicomponent heterocyclization; Switchable selectivity; Ultrasonic assisted reaction

Indexed keywords

5 AMINOPYRAZOLE; ACETAMIDE DERIVATIVE; ALDEHYDE; AMITROLE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; HEATING; MICROWAVE IRRADIATION; PRIORITY JOURNAL; SYNTHESIS; TEMPERATURE RELATED PHENOMENA; THERMODYNAMICS; ULTRASOUND;

EID: 80054872358     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.138     Document Type: Article

References (59)

1. (a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168;
2. (b) Dömling, A. Chem. Rev. 2006, 106, 17.
3. See, for example: (a) Alajarin, R.; Avarez-Buila, J.; Vaquero, J. J.; Sunkel, C.; Fau, J.; Statkov, P.; Sanz, J. Tetrahedron: Asymmetry 1993, 4, 617;
4. (b) Bossert, F.; Vater,W. Med. Res. Rev. 1989, 9, 291;
5. (c) Trigle, D. J.; Langs, D. A.; Janis, R. A. Med. Res. Rev. 1989, 9, 123;
6. (d) Tsuda, Y.; Mishina, T.; Obata, M.; Araki, K.; Inui, J.; Nakamura, T. WO 8,504,172, 1985; Chem. Abstr. 1986, 104, 207298;
7. (e) Tsuda, Y.; Mishina, T.; Obata, M.; Araki, K.; Inui, J.; Nakamura, T. JP 61,227,584, 1986; Chem. Abstr. 1988, 109,120988;
8. (f) Tsuda, Y.; Mishina, T.; Obata, M.; Araki, K.; Inui, J.; Nakamura, T. EP 0,217,142,1987; Chem. Abstr.1987,106, 213976;
9. (g) Atwal, K. S.; Vaccaro,W.; Lloyd, J.; Finlay, H.; Yan, L.; Bhandaru, R.S.WO 0,140,231, 2001; Chem. Abstr. 2003, 135, 19660;
10. (h) Atwal, K. S.; Moreland, S. Bioorg. Med. Chem. Lett.1991,1, 291;
11. (i) Kappe, C. O. Eur. J. Med. Chem. 2000, 35,1043;
12. (j) Ram, V. J.; Goel, A.; Sarkhel, S.; Maulik, P. R. Bioorg. Med. Chem. 2002, 10, 1275;
13. (k) Tenser, R. B.; Gaydos, A.; Hay, K. A. Antimicrob. Agents Chemother. 2001, 45, 3657;
14. (l) Gready, J. E.; McKinlay, C.; Gebauer, M. G. Eur. J. Med. Chem. 2003, 38, 719.
15. (a) Biggs-Houck, J. E.; Younai, A.; Shaw, J. T. Curr. Opin. Chem. Biol. 2010, 14, 371;
16. (b) Ganem, B. Acc. Chem. Res. 2009, 42, 463;
17. (c) Sunderhaus, J. D.; Martin, S. F. Chem.dEur. J. 2009, 15, 1300;
18. (d) Touré, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439;
19. (e) Colombo, M.; Peretto, I. Drug Discovery Today 2008, 13, 677;
20. (f) Isambert, N.; Lavilla, R. Chem.dEur. J. 2008, 14, 8444;
21. (g) Mironov, M. A. QSAR Comb. Sci. 2006, 25, 423;
22. Multicomponent Reactions; Zhu, J., Bienayme, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005;
23. (i) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471.
24. (a) Chebanov, V. A.; Gura, K. A.; Desenko, S. M. Top. Heterocycl. Chem. 2010, 23, 41;
25. (b) Chebanov, V. A.; Desenko, S. M.; Gurley, T. W. Azaheterocycles Based on a,b-Unsaturated Carbonyls; Springer: Meppel, 2008.
26. Chebanov, V. A.; Desenko, S. M. Curr. Org. Chem. 2006, 10, 297.
27. Desenko, S. M.; Orlov, V. D.; Getmanskii, N. V.; Shishkin, O. V.; Lindeman, S. V.; Struchkov, Y. T. Chem. Heterocycl. Compd. 1993, 29, 406.
28. (a) Wermann, K.; Hartman, M. Synthesis 1991, 189;
29. (b) Desenko, S. M.; Orlov, V. D.; Getmanskii, N. V.; Shishkin, O. V.; Lindeman, S. V.; Struchkov, Y. T. Dokl. Akad. Nauk 1992, 324, 801.
30. (a) Fedorova, O. V.; Zhidovinova,M.S.; Rusinov, G. L.;Ovchinnikova, I. G.Russ. Chem. Bull. 2003, 52,1768;
31. (b) Desenko, S. M.; Gladkov, E. S.; Nenaidenko, V. G.; Shishkin, O. V.; Shishkina, S. V. Chem. Heterocycl. Compd. 2004, 40, 65;
32. (c) Pryadeina, M. V.; Burgart, Y. V.; Saloutin, V. I.; Kodess, M. I.; Ulomskii, E. N.; Rusinov, V. L. Russ. J. Org. Chem. 2004, 40, 902;
33. Chebanov, V. A.;Muravyova, E. A.;Desenko, S.M.;Musatov, V. I.;Knyazeva, I. V.;Shishkina, S. V.;Shishkin, O. V.;Kappe, C. O. J.Comb.Chem.2006, 8, 427;
34. (e) Chernyshev, V. M.; Sokolov, A. N.; Taranushich, V. A. Russ. J. Appl. Chem. 2007, 80,1691;
35. (f) Shaabani, A.; Rahmati, A.; Rezayan, A. H.; Darvishi, M.; Badri, Z.; Sarvary, A. QSAR Comb. Sci. 2007, 26, 973;
36. (g) Song, L.; Cuihua, W.; Chenxia, V.; Shujiang, T. J. Heterocycl. Chem. 2008, 45,1609;
37. (h) Chen, Q.; Jiang, L.-L.; Chen, C.-N.; Yang, G.-F. J. Heterocycl. Chem. 2009, 46, 139.
38. (a) Sakhno, Y. I.; Shishkina, S. V.; Shishkin, O. V.; Musatov, V. I.; Vashchenko, E. V.; Desenko, S. M.; Chebanov, V. A. Mol. Diversity 2010, 9, 523;
39. (b) Sakhno, Y. I.; Desenko, S. M.; Shishkina, S. V.; Shishkin, O. V.; Sysoyev, D. O.; Groth, U.; Kappe, C. O.; Chebanov, V. A. Tetrahedron 2008, 64, 11041.
40. (a) Chebanov, V. A.; Sakhno, Y. I.; Desenko, S. M.; Shishkina, S. V.; Musatov, V. I.; Shishkin, O. V.; Knyazeva, I. V. Synthesis 2005, 2597;
41. (b) Chebanov, V. A.; Saraev, V. E.; Desenko, S. M.; Chernenko, V. N.; Shishkina, S. V.; Shishkin, O. V.; Kobzar, K. M.; Kappe, C. O. Org. Lett. 2007, 9, 1691;
42. (c) Chebanov, V. A.; Sakhno, Y. I.; Desenko, S. M.; Chernenko, V. N.; Musatov, V. I.; Shishkina, S. V.; Shishkin, O. V.; Kappe, C. O. Tetrahedron 2007, 63, 1229;
43. (d) Chebanov, V. A.; Saraev, V. E.; Desenko, S. M.; Chernenko, V. N.; Knyazeva, I. V.; Groth, U.; Glasnov, T. N.; Kappe, C. O. J. Org. Chem. 2008, 73, 5110;
44. (e) Muravyova, E. A.; Shishkina, S. V.; Musatov, V. I.; Shishkin, O. V.; Desenko, S. M.; Chebanov, V. A. Synthesis 2009, 1375;
45. (f) Gorobets, N. Y.; Sedash, Y. V.; Ostras, K. S.; Zaremba, O. V.; Shishkina, S. V.; Baumer, V. N.; Shishkin, O. V.; Kovalenko, S. M.; Desenko, S. M.; Van der Eycken, E. V. Tetrahedron Lett. 2010, 51, 2095;
46. (g) Rudenko, R. V.; Komykhov, S. A.; Desenko, S. M.; Musatov, V. I.; Shishkin, O. V.; Konovalova, I. S.; Vashchenko, E. V.; Chebanov, V. A. Synthesis 2011, 783;
47. (h) Sakhno, Y. I.; Desenko, S. M.; Shishkina, S. V.; Shishkin, O. V.; Musatov, V. I.; Chebanov, V. A. Synthesis 2011, 1120.
48. (a) Engler, T. A.; Chai, W.; Lynch, K. O., Jr. Tetrahedron Lett. 1995, 36, 7003;
49. (b) Cheng, H.-G.; Chen, C.-B.; Tan, F.; Chang, N.-J.; Chen, J.-R.; Xiao, W.-J. Eur. J. Org. Chem. 2010, 4976;
50. (c) Svélík, J.; Kettmann, V. Tetrahedron Lett. 2011, 52, 1062.
51. (a) Lipson, V. V.; Svetlichnaya, N. V.; Borodina, V. V.; Shirobokova, M. G.; Shishkina, S. V.; Shishkin, O. V.; Musatov, V. I. Russ. J. Org. Chem. 2010, 46, 1388;
52. (b) Hennig, L.; Hofmann, J.; Alva-Astudillo, M.; Mann, G. J. Prakt. Chem. 1990, 332, 351.
53. (a) Sitte, A.; Wessel, R.; Paul, H. Monatsh. Chem. 1975, 106, 1291;
54. (b) Desenko, S. M.; Orlov, V. D. Azaheterocycles Based on Aromatic Unsaturated Ketones; Folio: Kharkov, 1998;
55. (c) Kim, D. C.; Lee, Y. R.; Yang, B.-S.; Shin, K. J.; Kim, D. J.; Chung, B. Y.; Yoo, K. H. Eur. J. Med. Chem. 2003, 38, 525;
56. (d) Reddy, G. J.; Sailaja, S.; Manjula, D.; Rao, K. S.; Khalilullah, Md.; Latha, D. Heterocycl. Commun. 2005, 11, 385;
57. (e) Nam, N. L.; Grandberg, I. I.; Sorokin, V. I. Chem. Heterocycl. Compd. 2000, 36, 281;
58. (f) Miriyala, B.; Williamson, J. S. Tetrahedron Lett. 2003, 44, 7957.
59. Sheldrick, G. M. SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-Ray Diffraction Data. Rev.5.1, 1998.