DMAP-promoted cascade CeS/CeN bonds formation approach to 1,3-thiazolidin-4-ones via annulation of β-ketothioamides with α-halocarboxylic acids at room temperature

Tetrahedron

Volumn 70, Issue 39, 2014, Pages 6980-6984

  Verma, Girijesh Kumar ^a   Shukla, Gaurav ^a   Nagaraju, Anugula ^a   Srivastava, Abhijeet ^a   Singh, Maya Shankar ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

DCC; DMAP; One pot annulation; Thiazolidin 4 ones; Halocarboxylic acids; Ketothioamides

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; AMIDE; CARBON; CARBOXYLIC ACID DERIVATIVE; DICYCLOHEXYLCARBODIIMIDE; PROPIONIC ACID; SULFUR; THIAZOLIDINE DERIVATIVE; THIOAMIDE;

ANNULATION REACTION; ARTICLE; COVALENT BOND; ELECTROPHILICITY; NUCLEOPHILICITY; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION TIME; ROOM TEMPERATURE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 84922656056     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.07.084     Document Type: Article

References (65)

1. (a) Domino Reactions in Organic Synthesis; Tietze, L. F., Brasche, G., Gericke, K. M., Eds.; Wiley-VCH: Weinheim, Germany, 2006;
2. (b) Roca-Lopez, D.; Sadaba, D.; Delso, I.; Herrera, R. P.; Tejero, T.; Merino, P. Tetrahedron: Asymmetry 2010, 21, 2561-2601;
3. (c) Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314-325;
4. (d) Bonne, D.; Constantieux, T.; Coquerel, Y.; Rodriguez, J. Org. Biomol. Chem. 2012, 10, 3969-3973;
5. (e) Pellissier, H. Chem. Rev. 2013, 113, 442-524.
6. (a) Pozharskii, A. F.; Soldatenkov, A.; Katritzky, A. R. Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications, 2nd ed.; John Wiley & Sons: Chichester, U. K., 2011;
7. (b) Li, J. J. Heterocyclic Chemistry in Drug Discovery; John Wiley & Sons: Hoboken, N. J., 2013;
8. (c) Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; John Wiley & Sons: Chichester, U. K., 2010;
9. (d) For a special issue, see: Chem. Rev. 2004, 104, 1-6286.
10. (a) Brown, F. C. Chem. Rev. 1961, 61, 463-521;
11. (b) Singh, S. P.; Parmar, S. S.; Raman, K.; Stenberg, V. I. Chem. Rev. 1981, 81, 175-203;
12. (c) Jain, A. K.; Vaidya, A.; Ravichandran, V.; Kashaw, S. K.; Agrawal, R. K. Bioorg. Med. Chem. 2012, 20, 3378-3395;
13. (d) Cunico, W.; Gomes, C. R. B.; Vellasco, W. T., Jr. Mini-Rev. Org. Chem. 2008, 5, 336-344.
14. (a) Kumar, A.; Rajput, C. S.; Bhati, S. K. Bioorg. Med. Chem. 2007, 15, 3089-3096;
15. (b) Omar, K.; Geronikaki, A.; Zoumpoulakis, P.; Camoutsis, C.; Sokovic, M.; Ciric, A.; Glamoclija, J. Bioorg. Med. Chem. 2010, 18, 426-432;
16. (c) Prasad, D.; Kumar, A.; Shukla, P. K.; Nath, M. Org. Med. Chem. Lett. 2011, 1, 1-4;
17. (d) Kucukguzel, S. G.; Oruc, E. E.; Rollas, S.; Sahin, F.; Ozbek, A. Eur. J. Med. Chem. 2002, 37, 197-206;
18. (e) Chen, H.; Guo, Z.; Yin, Q.; Duan, X.; Gu, Y.; Li, X. Front. Chem. Sci. Eng. 2011, 5, 231-237;
19. (f) Rawal, R. K.; Tripathi, R.; Katti, S. B.; Pannecouque, C.; De Clercq, E. Bioorg. Med. Chem. 2007, 15, 1725-1731;
20. (g) Terzioglu, N.; Karali, N.; Gursoy, A.; Pannecouque, C.; Leysen, P.; Paeshuyse, J.; Neyts, J.; De Clercq, E. ARKIVOC 2006, i, 109-118.
21. (a) Miyata, Y.; Li, X.; Lee, H.-F.; Jinwal, U. K.; Srinivasan, S. R.; Seguin, S. P.; Young, Z. T.; Brodsky, J. L.; Dickey, C. A.; Sun, D.; Gestwicki, J. E. ACS Chem. Neurosci. 2013, 4, 930-939;
22. (b) Zarghi, A.; Najafnia, L.; Daraee, B.; Dadrass, O. G.; Hedayati, M. Bioorg. Med. Chem. Lett. 2007, 17, 5634-5637;
23. (c) Zebardast, T.; Zarghi, A.; Daraie, B.; Hedayati, M.; Dadrass, O. G. Bioorg. Med. Chem. Lett. 2009, 19, 3162-3165.
24. (a) Mao, J.; He, N.; Ning, Z.; Zhang, Q.; Guo, F.; Chen, L.; Wu, W.; Hua, J.; Tian, H. Angew. Chem., Int. Ed. 2012, 51, 9873-9876;
25. (b) Matsui, M.; Inoue, T.; Ono, M.; Kubota, Y.; Funabiki, K.; Jin, J.; Yoshida, T.; Higashijima, S.; Miura, H. Dyes Pigments 2013, 96, 614-618;
26. (c) Lebeuf, R.; Ferezou, I.; Rossier, J.; Arseniyadis, S.; Cossy, J. Org. Lett. 2009, 11, 4822-4825.
27. (a) Oecal, N.; Aydogan, F.; Yolacan, C.; Turgut, Z. J. Heterocycl. Chem. 2003, 40, 721-724;
28. (b) Haecker, H. G.; Elsinghorst, P. W.; Michels, S.; Daniels, J.; Schnakenburg, G.; Guetschow, M. Synthesis 2009, 1195-1203.
29. (a) Bolognese, A.; Correale, G.; Manfra, M.; Lavecchia, A.; Novellino, E.; Barone, V. Org. Biomol. Chem. 2004, 2, 2809-2813;
30. (b) Lingampalle, D.; Jawale, D.; Waghmare, R.; Mane, R. Synth. Commun. 2010, 40, 2397-2401.
31. (a) Borisevich, A. M.; Britsun, V. M.; Pirozhenko, V. V.; Lozinskii, M. O. Ukr. Khim. Zh. 2006, 72, 50-53;
32. (b) Jagodzinski, T. S.; Wesolowska, A.; Sosnicki, J. G. Pol. J. Chem. 2000, 74, 1101-1114;
33. (c) Zaleska, B.; Winnik, W. J. Prakt. Chem. 1989, 331, 55-60;
34. (d) Pratap, U. R.; Jawale, D. V.; Bhosle, M. R.; Mane, R. A. Tetrahedron Lett. 2011, 52, 1689-1691;
35. (e) Foroughifar, N.; Ebrahimi, S. Chin. Chem. Lett. 2013, 24, 389-391.
36. (a) Chowdhury, S.; Chanda, T.; Koley, S.; Ramulu, B. J.; Jones, R. C. F.; Singh, M. S. Org. Lett. 2013, 15, 5386-5389;
37. (b) Koley, S.; Chowdhury, S.; Chanda, T.; Ramulu, B. J.; Singh, M. S. Tetrahedron 2013, 69, 8013-8018;
38. (c) Samai, S.; Chanda, T.; Ila, H.; Singh, M. S. Eur. J. Org. Chem. 2013, 4026-4031;
39. (d) Singh, M. S.; Nandi, G. C.; Chanda, T. RSC Adv. 2013, 3, 14183-14198;
40. (e) Shukla, G.; Verma, G. K.; Nagaraju, A.; Verma, R. K.; Raghuvanshi, K.; Singh, M. S. RSC Adv. 2013, 3, 13811-13817;
41. (f) Singh, M. S.; Nagaraju, A.; Verma, G. K.; Shukla, G.; Verma, R. K.; Srivastava, A.; Raghuvanshi, K. Green Chem. 2013, 15, 954-962;
42. (g) Nandi, G. C.; Samai, S.; Singh, M. S. J. Org. Chem. 2010, 75, 7785-7795;
43. (h) Chowdhury, S.; Nandi, G. C.; Samai, S.; Singh, M. S. Org. Lett. 2011, 13, 3762-3765;
44. (i) Nandi, G. C.; Singh, M. S.; Ila, H.; Junjappa, H. Eur. J. Org. Chem. 2012, 967-974.
45. (a) Jagodzinski, T. S. Chem. Rev. 2003, 103, 197-227;
46. (b) (b)Wen, L.-R.; Shi, Y.-J.; Liu, G.-Y.; Li, M. J. Org. Chem. 2012, 77, 4252-4260;
47. (c) Wen, L.-R.; Ji, C.; Li, M.; Xie, H.-Y. Tetrahedron 2009, 65, 1287-1293;
48. (d) Li, M.; Hou, Y.-L.; Wen, L.-R.; Gong, F.-M. J. Org. Chem. 2010, 75, 8522-8532;
49. (e) Surmont, R.; Verniest, G.; Schrijver, M. D.; Thuring, J. W.; Holte, P. T.; Deroose, F.; Kimpe, N. D. J. Org. Chem. 2011, 76, 4105-4111;
50. (f) Mathew, P.; Asokan, C. V. Tetrahedron 2006, 62, 1708-1716;
51. (g) Samuel, R.; Chandran, P.; Retnamma, S.; Sasikala, K. A.; Sreedevi, N. K.; Anabha, E. R.; Asokan, C. V. Tetrahedron 2008, 64, 5944-5948;
52. (h) Wen, L.-R.; Sun, J.-H.; Li, M.; Sun, E.-T.; Zhang, S.-S. J. Org. Chem. 2008, 73, 1852-1863;
53. (i) Peruncheralathan, S.; Yadav, A. K.; Ila, H.; Junjappa, H. J. Org. Chem. 2005, 70, 9644-9647;
54. (j) Wen, L.-R.; He, T.; Lan, M.-C.; Li, M. J. Org. Chem. 2013, 78, 10617-10628;
55. (k) Verma, G. K.; Shukla, G.; Nagaraju, A.; Srivastav, A.; Raghuvanshi, K.; Singh, M. S. RSC Adv. 2014, 4, 11640-11647.
56. (a) Jagodzinski, T. S.; Westerlich, S. ARKIVOC 2013, iii, 294-303;
57. (b) Li, M.; Zuo, Z.; Wen, L.; Wang, S. J. Comb. Chem. 2008, 10, 436-441;
58. (c) Zaleska, B.; Burgiel, M. M.; Serda, P. Chem. Heterocycl. Compd. 2008, 44, 349-355;
59. (d) Fadda, A. A.; Abdel-Latif, E.; El-Mekawy, R. E. Eur. J. Med. Chem. 2009, 44, 1250-1256.
60. Wen, L.-R.; Men, L.-B.; He, T.; Ji, G.-J.; Li, M. Chem.dEur. J. 2014, 20, 5028-5033.
61. (a) Falco, J. L.; Pique, M.; Gonzalez, M.; Buira, I.; Mendez, E.; Terencio, J.; Perez, C.; Princep, M.; Palomer, A.; Guglietta, A. Eur. J. Med. Chem. 2006, 41, 985-990;
62. (b) Ma M., Paredes A., Bong D. J. Am. Chem. Soc. 2008 130, 14456-14458;
63. (c) Khan, I. U.; Zwanziger, D.; Boehme, I.; Javed, M.; Naseer, H.; Hyder, S. W.; Beck- Sickinger, A. G. Angew. Chem., Int. Ed. 2010, 49, 1155-1158;
64. (d) Brans, L.; Maes, V.; Garcia-Garayoa, E.; Schweinsberg, C.; Daepp, S.; Blauenstein, P.; Schubiger, P. A.; Schibli, R.; Tourwe, D. A. Chem. Biol. Drug Des. 2008, 72, 496-506.
65. The CCDC number for compound 3d is 971229, contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.