Facile synthesis of substituted thiophenes via Pd/C-mediated sonogashira coupling in water

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 24, 2006, Pages 6185-6189

  Raju, Sirisilla ^a,c   Kumar, P Rajender ^a   Mukkanti, K ^c   Annamalai, Pazhanimuthu ^b   Pal, Manojit ^b  

^a Custom Pharmaceutical Services   (India)

^b DR REDDY'S LABORATORIES LTD   (India)

^c JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

Aqueous media; Iodothiophene; Palladium catalyst; Terminal alkynes

Indexed keywords

ALKYNE; ANTINEOPLASTIC AGENT; THIOPHENE DERIVATIVE; WATER;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; SONOGASHIRA REACTION; SUBSTITUTION REACTION;

CARBON; INDICATORS AND REAGENTS; MACROCYCLIC COMPOUNDS; PALLADIUM; THIOPHENES; WATER;

EID: 33750698953     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.09.041     Document Type: Article

References (45)

1. Burger A. Prog. Drug Res. 37 (1991) 287
2. The diameter of the sulfur atom in thiophene is roughly equivalent to the distance between two neighboring carbon atoms in benzene and therefore both the aromatic rings are similar in size (isostere) and electronic properties.
3. Binder D., Hromatka O., Geissler F., Schmied K., and Noe C.R. J. Med. Chem. 30 (1987) 678
4. Foye W.O., and Tovivich S. J. Pharm. Sci. 68 (1979) 591
5. Bakker J., Gommers F.J., Nieuwenhuis I., and Wynberg H. J. Biol. Chem. 254 (1979) 1841
6. Iyengar S., Arnason J.T., Philogene B.J.R., Murand P., Werstink N.H., and Timmins G. Pestic. Biochem. Physiol. 29 (1987) 1
7. Matsuura H., Saxena G., Farmer S.W., Hancock R.E.W., and Towers G.H.N. Planta Med. 62 (1996) 65
8. Chan G.F.Q., Towers G.H.N., and Mitchell J.C. Phytochemistry 14 (1975) 2295
9. Hudson J.B., Graham E.A., Miki N., Towers G.H.N., Hudson L.L., Rossi R., Carpita A., and Neri D. Chemosphere 19 (1989) 1329
10. Zeni G., Nogueira C.W., Panatieri R.B., Silva D.O., Menezes P.H., Braga A.L., Silveira C.C., Stefani H.A., and Rocha J.B.T. Tetrahedron Lett. 42 (2001) 7921
11. For selected examples, see: in the case of uracil. Spector T., Porter D.J.T., Nelson D.J., Baccanari D.P., Davis S.T., Almond M.R., Khor S.P., Amyx H., Cao S., and Rustum Y.M. Drug Fut. 19 (1994) 565
12. Kundu N.G., Das B., Spears C.P., Majumdar A., and Kang S.I. J. Med. Chem. 33 (1990) 1975
13. Kundu N.G., Dasgupta S.K., Chaudhuri L.N., Mahanty J.S., Spears C.J., and Shahinian A.H. Eur. J. Med. Chem. 28 (1993) 473
14. For pyrone:. Marrision L.R., Dickinson J.M., Ahmed R., and Fairlamb I.J.S. Tetrahedron Lett. 43 (2002) 8853
15. Marrision L.R., Dickinson J.M., and Fairlamb I.J.S. Bioorg. Med. Chem. Lett. 12 (2002) 3509
16. Fairlamb I.J.S., Lu F.-J., and Schmidt J.-P. Synthesis (2003) 2564
17. Fairlamb I.J.S., Marrison L.R., Dickinson J.M., Lu F.-J., and Schmidt J.-P. Bioorg. Med. Chem. 12 (2004) 4285
18. Lee J.-H., Park J.-S., and Cho C.-G. Org. Lett. 4 (2002) 1171
19. For purin. Hocek M., and Votruba I. Bioorg. Med. Chem. Lett. 12 (2002) 1055
20. For adenosine. Volpini R., Costanzi S., Lambertucci C., Vittori S., Klotz K.-N., Lorenzen A., and Cristalli G. Bioorg. Med. Chem. Lett. 11 (2001) 1931
21. Cristalli G., Camaioni E., Vittori S., Volpini R., Borea P.A., Conti A., Dionisotti S., Ongini E., and Monopoli A. J. Med. Chem. 38 (1995) 1462
22. For quinolines:. Nolan J.M., and Comins D.L. J. Org. Chem. 68 (2003) 3736
23. Raju S., Batchu V.R., Swamy N.K., Dev R.V., Babu J.M., Kumar P.R., Mukkanti K., and Pal M. Tetrahedron Lett. 47 (2006) 83
24. Raju S., Batchu V.R., Swamy N.K., Dev R.V., Sreekanth B.R., Babu J.M., Vyas K., Kumar P.R., Mukkanti K., Annamalai P., and Pal M. Tetrahedron 62 (2006) 9554
25. Nieves-Neira W., Rivera M.I., Kohlhagen G., Hursey M.L., Pourquier P., Sausville E.A., and Pommier Y. Mol. Pharmacol. 56 (1999) 478
26. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. 16 (1975) 4467
27. Nikolai A.B., Ludmila I.S., Elena V.L., Tatiana P.T., and Irina P.B. Tetrahedron Lett. 37 (1996) 897
28. Van den Hoven B.G., and Alper H. J. Org. Chem. 64 (1999) 9640 and references cited therein.
29. Oh C.H., and Reddy V.R. Synlett 12 (2004) 2091
30. For preparation via Cu-free Sonogashira coupling in ionic liquid, see:. Fukuyma T., Shinmen M., Nishitani S., Sato M., and Ryu I. Org. Lett. 4 (2002) 1691
31. For preparation via Sonogashira coupling using controlled microwave heating, see:. Erdelyl M., and Gogoll A. J. Org. Chem. 66 (2001) 4165
32. Batchu V.R., Subramanian V., Parasuraman K., Swamy N.K., Kumar S., and Pal M. Tetrahedron 61 (2005) 9869
33. See also:. Pal M., Subramanian V., Batchu V.R., and Dager I. Synlett (2004) 1965
34. Pal M., Subramanian V., and Yeleswarapu K.R. Tetrahedron Lett. 44 (2003) 8221
35. 2); UV (nm, MeOH) 359.8, 269.2, 202.4; HPLC 99.0%, column: Zorbax Eclipse XDB C-18 (150 × 4.6) mm, mobile phase A: 0.05% TFA in water, mobile phase B: 0.05% TFA in methanol, gradient (T/%B): 0/30, 13/70, 15/100, 25/100, flow rate: 1.5 mL/min, UV 254 nm, retention time 17.1 min.
36. The compound 1b was prepared according to the following Scheme {A figure is presented} see:. Campaigne E., and Monroe P.A. J. Am. Chem. Soc. 76 (1954) 2447
37. Ishikawa T., Mizutani A., Miwa C., Oku Y., Komano N., Takami A., and Watanabe T. Heterocycles 45 (1997) 2261
38. For further mechanistic discussion, see:. Pal M., Subramanian V., Parasuraman K., and Yeleswarapu K.R. Tetrahedron 59 (2003) 9563
39. Subramanian V., Batchu V.R., Barange D., and Pal M. J. Org. Chem. 70 (2005) 4778
40. Kloetzel M.C., Little J.E., and Frisch Jr. D.M. J. Org. Chem. 18 (1953) 1511
41. Asprou C.M., Brunskill J.S.A., Jeffrey H., and De A. J. Heterocyl. Chem. 17 (1980) 87
42. Napier R.P., Kaufman H.A., and Driscoll P.R. J. Heterocyl. Chem. 7 (1970) 393
43. The 4-keto-4,5,6,7-tetrahydrothianaphthene is a key intermediate for the synthesis of a range of sulfur-containing compounds, see:. Mosti L., Schenone P., Menozzi G., and Romussi G. J. Heterocyl. Chem. 19 (1982) 1057 See also Ref. 19a-b.
44. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Wolff A., Gray-Goodrich M., Campbell H., Mayo J., and Boyd M. J. Natl. Cancer Inst. 83 (1991) 757
45. For protocol for in vitro cell growth assay, please see Ref. 12b.