A facile IL-DMSO assisted synthesis of 5-, 6-, and 7-membered benzo-annelated cyclic guanidines

Tetrahedron Letters

Volumn 53, Issue 24, 2012, Pages 2954-2958

  Verma, Amit ^a   Giridhar, Rajani ^a   Modh, Pratik ^a   Yadav, Mange Ram ^a  

^a M S UNIVERSITY OF BARODA   (India)

Author keywords

2 Imino 4 quinazolinone; Cyanogen bromide; Cyclic guanidine; DMSO; Ionic liquids

Indexed keywords

2 AMINOBENZIMIDAZOLE; 2 IMINO 4 QUINAZOLINONE; 2 IMINO 5 BENZOTRIAZ EPINONE; DIMETHYL SULFOXIDE; GUANIDINE DERIVATIVE; IONIC LIQUID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENVIRONMENTAL TEMPERATURE; MICROWAVE IRRADIATION;

EID: 84861200977     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.03.060     Document Type: Article

References (40)

1. R.G.S. Berlinck Prog. Chem. Org. Nat. Prod. (Fortsch. Chem. Org. Naturst.) 66 1995 339
2. R.G.S. Berlinck Nat. Prod. Rep. 13 1996 377
3. R.G.S. Berlinck Nat. Prod. Rep. 16 1999 339
4. R.G.S. Berlinck Nat. Prod. Rep. 19 2002 617
5. R.G.S. Berlinck, and M.H. Kossuga Nat. Prod. Rep. 22 2005 516
6. L. Heys, C.G. Moore, and P. Murphy J. Chem. Soc. Rev. 29 2000 57
7. R.G.S. Berlinck, A.C.B. Burtoloso, and M.H. Kossuga Nat. Prod. Rep. 25 2008 919
8. L.D. Via, O. Gia, S.M. Magno, A.D. Settimo, A.M. Marini, G. Primofiore, F.D. Settimo, and S. Salerno IL Farmaco 56 2001 159
9. G.E. Hardtmann, G. Koletar, O.R. Pfister, J.H. Gogerty, and L.C. Iorio J. Med. Chem. 18 1975 447
10. V. Alagarsamy, and U.S. Pathak Bioorg. Med. Chem. 15 2007 3457
11. W.H.W. Lunn, R.W. Harper, and R.L. Stone J. Med. Chem. 14 1971 1069
12. W. Pendergast, J.V. Johnson, S.H. Dickerson, I.K. Dev, D.S. Duch, R. Ferone, W.R. Hall, J. Humphrey, J.M. Kelly, and D.C. Wilson J. Med. Chem. 36 1993 2279
13. J.-W. Chern, P.-L. Tao, K.-C. Wang, A. Gutcait, S.-W. Liu, M.-H. Yen, S.-L. Chien, and J.-K. Rong J. Med. Chem. 41 1998 3128
14. J.A. Grosso, E.D. Nichols, J.D. Kohli, and D. Glock J. Med. Chem. 25 1982 703
15. F. Somers, R. Ouedraogo, M.-H. Antoine, P. de Tullio, B. Becker, J. Fontaine, J. Damas, L. Dupont, B. Rigo, J. Delarge, P. Lebrun, and B. Pirotte J. Med. Chem. 44 2001 2575
16. V. Alagarsamy, K. Dhanabal, P. Parthiban, G. Anjana, G. Deepa, B. Murugesan, S. Rajkumar, and A.J. Beevi J. Pharm. Pharmacol. 59 2007 669
17. P. Párkányi, H.L. Yuan, B.H.E. Strömberg, and E. Evenzahav J. Heterocycl. Chem. 29 1992 749 753
18. C. Tun-Cheng, C. Chien-Shu, Y.U. Fang-Hwa, and C. Ji-Wang Chem. Pharm. Bull. 52 2004 1422 1426
19. M.A. El-Hashash, D.B. Guirguis, and Y.A. El-Badry Pharm. Chem. 3 2011 147 159
20. J.F. Wolfe, T.L. Rathman, M.C. Sleevi, J.A. Campbell, and T.D. Greenwood J. Med. Chem. 33 1990 161 166
21. A. Kumar, S. Sharma, Archana, K. Bajaj, S. Sharma, H. Panwar, T. Singh, and V.K. Srivastava Bioorg. Med. Chem. 11 2003 5293 5299
22. B.R. Copp, C.R. Fairchild, L. Cornell, A.M. Casazza, S. Robinson, and C.M. Ireland J. Med. Chem. 41 1998 3909 3911
23. I.M. McDonald, J.W. Black, I.M. Buck, D.J. Dunstone, E.P. Griffin, E.A. Harper, R.A.D. Hull, S.B. Kalindjian, E.J. Lilley, I.D. Linney, M.J. Pether, S.P. Roberts, M.E. Shaxted, J. Spencer, K.I.M. Steel, D.A. Sykes, M.K. Walker, G.F. Watt, L. Wright, P.T. Wright, and W. Xun J. Med. Chem. 50 2007 3101 3112
24. G.S. Babu, N. Rajani, S.P. Malathy, B. Srinivas, U. Kulandaivelu, and J.V. Rao Pharm. Chem. 2 2010 196 204
25. R.W. Leiby, and N.D. Heindel J. Pharm. Sci. 66 1977 605 606
26. C. Bischoff, and E. Schroeder J. Fuer. Prakt. Chem. 325 1983 88 94
27. K.R. Seddon J. Chem. Technol. Biotechnol. 68 1997 351
28. D. Bradley Chem. Ind. 86 1999 445
29. T. Welton Chem. Rev. 99 1999 2071
30. L. Blanchard, D. Hancu, E.J. Beckmann, and J.F. Brennecke Nature 399 1999 28
31. S. Dai, Y.H. Ju, and C.E. Barner J. Chem. Soc., Dalton Trans. 1999 1201
32. J.G. Hudelston, H.D. Willauer, R.P. Swatloski, A.E. Visser, and R.D. Rogers Chem. Commun. 1998 1765
33. Yadav, M. R.; Grande, F.; Chouhan, B. S.; Naik, P. P.; Giridhar, R.; Garofalo, A.; Neamati, N. Eur. J. Med. Chem., in press, Available online 21 December 2011.
34. M. Freemantle Chem. Eng. News 76 1998 32
35. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis 2nd ed. 2007 VCH-Wiley Weinheim, Germany
36. A. Wierzbicki, and J.H. Davis Jr. Proceedings of the Symposium on Advances in Solvent Selection and Substitution for Extraction, March 5-9, 2000, Atlanta, Georgia 2000 AIChE New York
37. S.N. Dighe, R.V. Bhattad, R.R. Kulkarni, K.S. Jain, and K.V. Srinivasan Synth. Commun. 40 2010 3522 3527
38. S.N. Dighe, K.S. Jain, and K.V. Srinivasan Tetrahedron Lett. 50 2009 6139 6142
39. K. Dong, S. Zhang, D. Wang, and X. Yao J. Phys. Chem. A 110 2006 9775 9782
40. J. Thar, M. Brehm, A.P. Seitsonen, and B. Kirchner J. Phys. Chem. B Lett. 113 2009 15129 15132