An efficient conjugate hydrothiocyanation of chalcones with a task-specific ionic liquid

Tetrahedron Letters

Volumn 48, Issue 44, 2007, Pages 7793-7795

  Yadav, Lal Dhar S ^a   Patel, Rajesh ^a   Rai, Vijai K ^a   Srivastava, Vishnu P ^a  

^a UNIVERSITY OF ALLAHABAD   (India)

Author keywords

1,3 Thiazines; Chalcones; Conjugate addition; Hydrothiocyanation; Ionic liquids; Thiocyanates

Indexed keywords

1 N BUTYL 3 METHYLIMIDAZOLIUM THIOCYANATE; 2 AMINO 1,3 THIAZINE DERIVATIVE; AMINE; CHALCONE DERIVATIVE; IONIC LIQUID; THIAZINE DERIVATIVE; THIOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONJUGATION; CYANATION; HYDROTHIOCYANATION; MOLECULAR INTERACTION; ONE POT SYNTHESIS; REACTION ANALYSIS;

EID: 34848922076     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.024     Document Type: Article

References (37)

1. Kelly T.R., Kim M.H., and Curtis A.D.M. J. Org. Chem. 58 (1993) 5855-5857
2. Metzer J.B. In: Katritzky A. (Ed). Comprehensive Heterocyclic Chemistry Vol. 6 (1984), Pergamon, Oxford 235
3. Leblanc B.L., and Jursic B.C. Synth. Commun. 28 (1998) 3591-3599
4. Newman A.A. Chemistry and Biochemistry of Thiocyanic Acid and its Derivatives (1975), Academic Press
5. Mehta R.G., Liu J., Constantinou A., Thomas C.F., Hawthorne M., You M., Gerhaeusers C., Pezzuto J.M., Moon R.C., and Moriarty R.M. Carcinogenesis 16 (1995) 399-404
6. Guy R.G. In: Patai S. (Ed). The Chemistry of Cyanates and Their Thio Derivatives (1977), Wiley, New York 819
7. Bacon R.G.R., and Guy R.G. J. Chem. Soc. (1961) 2428-2447
8. Tamura Y., Kawasaki T., Adachi M., Tonio M., and Kita Y. Tetrahedron Lett. 18 (1977) 4417-4420
9. Burski J., Kiesowski J., Michalski J., Pakulski M., and Skowronska A. Tetrahedron 39 (1983) 4175-4181
10. Iranpoor N., Firouzabadi H., and Shaterian H. Synlett (2000) 65-66
11. Molina P., Alajarin M., Ferao A., Lindon M.J., Fresneda P.M., and Vilaplana M.J. Synthesis (1982) 472-479
12. Renard P.Y., Schwebel H., Vayron P., Leclerc E., Dais S., and Mioskowski C. Tetrahedron Lett. 42 (2001) 8479-8481
13. Prakash O., Kaur H., Batra H., Rani N., Singh S.P., and Moriarty R.M. J. Org. Chem. 66 (2001) 2019-2023
14. Chowdhury S., Mohan R.S., and Scott J.L. Tetrahedron 63 (2007) 2363-2389
15. Bao W., and Wang Z. Green Chem. 8 (2006) 1028-1033
16. Zhao D., Wu M., Kou Y., and Min E. Catal. Today 74 (2002) 157-189
17. Dupont J., de Souza R.F., and Suarez P.A.Z. Chem. Rev. 102 (2002) 3667-3692
18. Qiao K., and Yakoyama C. Chem. Lett. 33 (2004) 472-473
19. Sun W., Xia C.-G., and Wang H.-W. Tetrahedron Lett. 44 (2003) 2409-2411
20. Kamal A., and Chouhan G. Tetrahedron Lett. 46 (2005) 1489-1491
21. Earle M.J., Ktdare S.P., and Seddon K.R. Org. Lett. 6 (2004) 707-710
22. Baudequin C., Boudoux J., Levllain J., Cahard D., Gaumont A.-C., and Plaquevent J.-C. Tetrahedron: Asymmetry 14 (2003) 3081-3093
23. Madkour H.M.F., Salem M.A.I., Soliman E.A., and Mahmoud N.F.H. Phosphorus, Sulfur, Silicon, Relat. Elem. 170 (2001) 15-27
24. Yadav L.D.S., Awasthi C., Rai V.K., and Rai A. Tetrahedron Lett. 48 (2007) 4899-4902
25. Yadav L.D.S., Rai A., Rai V.K., and Awasthi C. Synlett (2007) 1905-1908
26. Yadav L.D.S., Yadav S., and Rai V.K. Green Chem. 8 (2006) 455-458
27. Yadav L.D.S., Yadav S., and Rai V.K. Tetrahedron 61 (2005) 10013-10017
28. Yadav L.D.S., and Kapoor R. J. Org. Chem. 69 (2004) 8118-8120
29. 12ClNOS: C, 63.68; H, 4.01; N, 4.64. Found: C, 63.97; H, 4.33; N, 4.28.
30. Kai H., Morioko Y., Tomida M., Takahashi T., Hattori M., Hanasaki K., Koike K., Chiba H., Shinohara S., and Kanemasa T. Bioorg. Med. Chem. Lett. 17 (2007) 3925-3929
31. Glasnov T.N., Vugts D.J., Koningstein M.M., Desai B., Fabian W.M.F., Orru R.V.A., and Kappe C.O. QSAR Combinatorial Sci. 25 (2006) 509-518
32. Calaycay J.R., Kelly T.M., MacNaul K.L., McCauley E.D., Qi H., Grant S.K., Griffin P.R., and Hutchinson N.I. J. Biol. Chem. 271 (1996) 28212-28219
33. Canjolle R., Hamid A., Payard M., Loiseau P.R., Bories C., Loiseau P.M., and Gayral P. Eur. J. Med. Chem. 24 (1989) 287-291
34. 2S: C, 70.11; H, 4.55; N, 7.43. Found: C, 70.37; H, 4.39; N, 7.51.
35. Takamizawa A., and Hirai K. J. Org. Chem. 30 (1965) 2290-2296
36. Ingarsal N., Amutha P., and Nagarajan S. J. Sulfur Chem. 27 (2006) 455-459
37. El-hashash M.A., El-nagdy S., and Amine M.S. Phosphorus, Sulfur, Silicon, Relat. Elem. 55 (1991) 279-283