Synthesis of new amidino-substituted 2-aminothiophenoles: mild basic ring opening of benzothiazole

Tetrahedron

Volumn 64, Issue 51, 2008, Pages 11594-11602

  Racané, Livio ^a   Tralić Kulenović, Vesna ^a   Mihalić, Zlatko ^b   Pavlović, Gordana ^a   Karminski Zamola, Grace ^c  

^a UNIVERSITY OF ZAGREB   (Croatia)

^b UNIVERSITY OF ZAGREB   (Croatia)

^c UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

Amidine; Benzothiazole; Disulfide; Pinner reaction; Thiolate

Indexed keywords

3,3' DISULFANEDIYLBIS (4 AMINOBENZOIC ACID); 3,3' DISULFANEDIYLBIS [4 AMINOBENZO (IMIDAZOLINIUM 2 YL CHLORIDE)]DIHYDRATE; 3,3' DISULFANEDIYLBIS [4 AMINOBENZO (N ISOPROPYL AMIDINIUM CHLORIDE)]DIHYDRATE; 3,3' DISULFANEDIYLBIS(4 AMINOBENZOCARBOXAMIDINIUM CHLORIDE)DIHYDRATE; 5 (IMIDAZOLINIUM 2 YL) 2 AMINOBENZOTHIOLATE HYDRATE; 5 AMIDINIUM 2 AMINOBENZOTHIOLATE; 6 (IMIDAZOLIN 2 YL)BENZOTHIAZOLE HYDROCHLORIDE HYDRATE; 6 (N ISOPROPYLAMIDINO)BENZOTHIAZOLE HYDROCHLORIDE; 6 AMIDINOBENZOTHIAZOLE HYDROCHLORIDE DIHYDRATE; AMPHOLYTE; BENZOTRIAZOLE DERIVATIVE; DISULFIDE; THIOPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PINNER REACTION; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 55549086117     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.026     Document Type: Article

References (49)

1. Leong C.O., Suggitt M., Swaine D.J., Bibby M.C., Stevens M.F.G., and Bradshaw T.D. Mol. Cancer Ther. 3 (2004) 1565-1575
2. Yldiz-Oren I., Yalcin I., Aki-Sener E., and Ucarturk N. Eur. J. Med. Chem. 39 (2004) 291-298
3. Sheng C., Zhu J., Zhang W., Zhang M., Ji H., Song Y., Xu H., Yao J., Miao Z., Zhou Y., Zhu J., and Lu J. Eur. J. Med. Chem. 42 (2007) 477-486
4. Lochart A., Ye L., Judd D.B., Merritt A.T., Lowe P.N., Morgenstern J.L., Hong G., Gee A.D., and Brown J. J. Biol. Chem. 280 (2005) 7677-7684
5. Grout R.J. In: Patai S. (Ed). The Chemistry of Amidines and Imidates Vol. 1 (1975), Wiley & Sons, New York, NY p 255-281
6. Tidwell R.R., and Boykin D.W. In: Demeunynck M., Bailly C., and Wilson W.D. (Eds). Small Molecule DNA and RNA Binders Vol. 2 (2003), Wiley-VCH, Weinheim p 414-501
7. Munde M., Ismail M.A., Arafa R., Peixoto P., Collar C.J., Liu Y., Hu L., David-Cordonnier M.-H., Lansiaux A., Bailly C., Boykin D.W., and Wilson W.D. J. Am. Chem. Soc. 129 (2007) 13732-13743
8. Arafa R.K., Brun R., Wenzler T., Tanious F.A., Wilson W.D., Stephens C.E., and Boykin D.W. J. Med. Chem. 48 (2005) 5480-5488
9. Metzger J., and Plank H. Chim. Ind. 75 (1956) 929-939
10. Metzger J., and Plank H. Chim. Ind. 75 (1956) 1290-1303
11. Jacobson P. Chem. Ber. 19 (1886) 1067-1078
12. Spitulnik M.J. Synthesis (1976) 730-731
13. Bowman W.R., Heaney H., and Jordan B.M. Tetrahedron 47 (1991) 10119-10128
14. Jayanthi G., Muthusamy S., Paramasivam R., Ramakrishnan V.T., Ramasamy N.K., and Ramamurthy P. J. Org. Chem. 62 (1997) 5766-5770
15. Stanetty P., and Krumpak B. J. Org. Chem. 61 (1996) 5130-5133
16. Spyros M., Gatos D., and Barlos K. Tetrahedron Lett. 42 (2001) 2201-2204
17. Evindar G., and Batey R.A. J. Org. Chem. 71 (2006) 1802-1808
18. Bose D.S., and Idrees M. Tetrahedron Lett. 48 (2007) 669-672
19. Batista R.M.F., Costa S.P.G., Malheiro E.L., Belsley M., and Raposo M.M.M. Tetrahedron 63 (2007) 4258-4265
20. Downer-Riley N.K., and Jackson Y.A. Tetrahedron (2008) 7741-7744
21. Boyd G.V. In: Patai S., and Rappoport Z. (Eds). The Chemistry of Amidines and Imidates Vol. 2 (1991), Wiley & Sons, New York, NY p 339-365
22. Cai L., Han Y., Ren S., and Huang L. Tetrahedron 56 (2000) 8253-8262
23. Yin Z., Zhang Z., Zhu J., Wong H., Kadow J.F., Meanwell N.A., and Wang T. Tetrahedron Lett. 46 (2005) 4919-4923
24. Gargipati S.R. Tetrahedron Lett. 31 (1990) 1969-1972
25. Rousselt G., Capdevielle P., and Maumy M. Tetrahedron Lett. 34 (1993) 6395-6398
26. Gielen H., Alonso-Alija C., Hendrix M., Niewohner U., and Schauss D. Tetrahedron Lett. 43 (2002) 419-421
27. Schaefer F.C., and Peters G.A. J. Org. Chem. 26 (1961) 412-418
28. Hranjec M., Kralj M., Piantanida I., Sedić M., Šuman L., Pavelić K., and Karminski-Zamola G. J. Med. Chem. 50 (2007) 5696-5711
29. Starčević K., Kralj M., Ester K., Sabol I., Grce M., Pavelić K., and Karminski-Zamola G. Bioorg. Med. Chem. 15 (2007) 4419-4426
30. Racanè L., Tralić-Kulenović V., Kitson R.P., and Karminski-Zamola G. Monatsh. Chem. 137 (2006) 1571-1577
31. Racanè L., Tralić-Kulenović V., Fišer-Jakić L., Boykin W.D., and Karminski-Zamola G. Heterocycles 55 (2001) 2085-2098
32. Racanè L., Tralić-Kulenović V., Boykin W.D., and Karminski-Zamola G. Molecules 8 (2003) 342-349
33. Tralić-Kulenović V., Karminski-Zamola G., Racanè L., and Fišer-Jakić L. Heterocycl. Commun. 4 (1998) 423-428
34. Matković-Čalogović D., Popović Z., Tralić-Kulenović V., Racanè L., and Karminski-Zamola G. Acta Crystallogr. C59 (2003) o190-o191
35. Allen F.H., Kennard O., Watson D.G., Brammer L., Orpen A.G., and Taylor R. J. Chem. Soc., Perkin Trans. 2 (1987) S1-S19
36. Lang R.C., Williams C.M., and Garson M.J. Org. Prep. Proced. Int. 35 (2003) 520-524
37. Metzger J. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 6 (1984), Pergamon, Oxford p 235-231
38. Bartoli G., Ciminale F., and Todesco P.E. Tetrahedron Lett. 16 (1975) 1785-1786
39. Bartoli G., Lelli M., Ciminale F., and Attanasi O. J. Chem. Soc., Perkin Trans. 2 (1977) 20-24
40. Chedekel M.R., Sharp D.E., and Jeffery G.A. Synth. Commun. (1980) 167-173
41. Shorter J. In: Patai S., and Rappoport Z. (Eds). The Chemistry of Amidines and Imidates Vol. 2 (1991), Wiley & Sons, New York, NY p 689-705
42. Taylor E.C., and Ehrhart W.A. J. Am. Chem. Soc. 82 (1960) 3138-3141
43. Trinajstić N. Tetrahedron Lett. 12 (1968) 1529-1532
44. Field L. In: Oae S. (Ed). Organic Chemistry of Sulfur (1977), Plenum, New York, NY 303-382
45. Boggust W.A., and Cocker W. J. Chem. Soc. (1949) 355-361
46. Oxford Diffraction. Xcalibur CCD System, CrysAlis Software System, Version 171.23 (2004), Oxford Diffraction, Abingdon, UK
47. Sheldrick G.M. Acta Crystallogr. A64 (2008) 112-122
48. Spek A.L. Acta Crystallogr. A46 (1990) 34
49. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision D02 (2004), Gaussian, Wallingford, CT