Hetero-Diels-Alder reaction of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with arylsulfonylcyanides. Synthesis and antimicrobial activity of 4-hydroxy-2-(arylsulfonyl)pyridines

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 23, 2008, Pages 9898-9903

  Hussain, Ibrar ^a   Yawer, Mirza Arfan ^a   Lalk, Michael ^b   Lindequist, Ulrike ^b   Villinger, Alexander ^a   Fischer, Christine ^c   Langer, Peter ^a,c  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b UNIVERSITY OF GREIFSWALD   (Germany)

^c LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Antimicrobial activity; Cyclizations; Pyridines; Silyl enol ethers

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 2 ETHOXY 3 FLUORO 6 (PHENYLSULFONYL)PYRIDIN 4 OL; 2 ETHOXY 3 FLUORO 6 TOSYLPYRIDIN 4 OL; 2 METHOXY 6 (PHENYLSULFONYL) 3 (PHENYLTHIO)PYRIDIN 4 OL; 2 METHYL 3 (3 TOLYLOXY) 6 TOSYLPYRIDIN 4 OL; 2 METHYL 3 (4 TOLYLOXY) 6 TOSYLPYRIDIN 4 OL; 2 METHYL 3 (4 TOLYLTHIO) 6 TOSYLPYRIDIN 4 OL; 2 METHYL 3 (PHENYLTHIO) 6 TOSYLPYRIDIN 4 OL; 2 METHYL 6 (PHENYLSULFONYL) 3 (3 TOLYLTHIO)PYRIDIN 4 OL; 2 METHYL 6 (PHENYLSULFONYL) 3 (PHENYLTHIO)PYRIDIN 4 OL; 3 (3,5 DIMETHYLPHENOXY) 2 ETHOXY 6 (PHENYLSULFONYL)PYRIDIN 4 OL; 3 (3,5 DIMETHYLPHENOXY) 2 ETHOXY 6 TOSYLPYRIDIN 4 OL; 3 CHLORO 2 ETHOXY 6 (PHENYLSULFONYL)PYRIDIN 4 OL; 3 CHLORO 2 ETHOXY 6 TOSYLPYRIDIN 4 OL; 3 ETHYL 2 METHOXY 6 (PHENYLSULFONYL)PYRIDIN 4 OL; AMPICILLIN; CYANIDE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CANDIDA; CONTROLLED STUDY; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; GRAM POSITIVE BACTERIUM; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; BACILLUS SUBTILIS; BUTADIENES; CANDIDA; CYANIDES; CYCLIZATION; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; PYRIDINES; STAPHYLOCOCCUS AUREUS;

ALNUS; POSIBACTERIA;

EID: 55749098625     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.10.033     Document Type: Article

References (83)

1. For a review of applications of nitriles as reagents for organic synthesis with loss of the nitrile functionality (including cycloaddition reactions), see. Collier S., and Langer P. Science of Synthesis. In: Shinkai I., and Murahashi S. (Eds) (2004), Thieme, Stuttgart Chapter 19.5.15
2. For examples from our laboratory, see. Langer P., and Appel B. Tetrahedron Lett. (2003) 5133
3. Blank J., Kandt M., Pfeiffer W.-D., Hetzheim A., and Langer P. Eur. J. Org. Chem. (2003) 182
4. Langer P., and Bodtke A. Tetrahedron Lett. (2003) 5965
5. Langer P., and Bodtke A. Synlett (2003) 1743
6. Langer P., and Albrecht U. Synlett (2003) 1503
7. Langer P., Döring M., Schreiner P.R., and Görls H. Chem. Eur. J. 7 (2001) 2617
8. Langer P., Döring M., and Seyferth D. Chem. Commun. (1998) 1927
9. Langer P., Döring M., Seyferth D., and Görls H. Eur. J. Org. Chem. (2003) 1948
10. Bönnemann H. Angew. Chem. Int. Ed. Engl. 17 (1978) 505
11. Bönnemann H., Brinkmann R., and Schenkluhn H. Synthesis (1974) 575
12. Bönnemann H., and Brijoux W. Adv. Heterocycl. Chem. 48 (1990) 177
13. Naiman A., and Vollhardt K.P.C. Angew. Chem. Int. Ed. Engl. 16 (1977) 708
14. Hillard III R.L., Parnell C.L., and Vollhardt K.P.C. Tetrahedron 39 (1983) 905
15. Geiger R.E., Lalonde M., Stoller H., and Schleich K. Helv. Chim. Acta (1984) 1274
16. Parnell C.A., and Vollhardt K.P.C. Tetrahedron 41 (1985) 5791
17. Yamamoto Y., Okuda S., and Itoh K. J. Chem. Soc., Chem. Commun. (2001) 1102
18. Varela J.A., Castedo L., and Saa C. J. Am. Chem. Soc. 120 (1998) 12147
19. Fatland A.W., and Eaton B.E. Org. Lett. 2 (2000) 3131
20. Heller B., Sundermann B., Buschmann H., Drexler H.-J., You J., Holzgrabe U., Heller E., and Oehme G. J. Org. Chem. 67 (2000) 4414
21. Suzuki D., Tanaka R., Urabe H., and Sato F. J. Am. Chem. Soc. 124 (2002) 3518
22. Takahashi T., Tsai F.-Y., and Kotora M. J. Am. Chem. Soc. 122 (2000) 4994
23. Takahashi T., Tsai F.-Y., Li Y., Wang H., Kondo Y., Yamanaka M., Nakajima K., and Kotora M. J. Am. Chem. Soc. 124 (2002) 5059
24. Yang N.-C.C., Kim B., Chiang W., and Hamada T. J. Chem. Soc., Chem. Commun. (1976) 729
25. Cantrell T.S. J. Am. Chem. Soc. 94 (1972) 5929
26. Cantrell T.S. J. Org. Chem. (1977) 4238
27. Arbuzov B.A., and Zobova N.N. Izv. Akad. Nauk. SSSR, Ser. Khim. (1972) 2325
28. Dunica J.V., Pierce M.E., and Santella III J.B. J. Org. Chem. 56 (1991) 2395
29. Wittenberger S.J., and Donner B.G. J. Org. Chem. 58 (1993) 4139
30. Curran D.P., Hadida S., and Kim S.Y. Tetrahedron 55 (1999) 8997
31. Wiberg V.E., and Michaud H.Z. Z. Naturforsch. Teil B 9 (1954) 497
32. Huff B.E., and Staszak M.A. Tetrahedron Lett. 34 (1993) 8011
33. Kumar A., Narayanan R., and Shechter H. J. Org. Chem. 61 (1996) 4462
34. Mihina J.S., and Herbst R.M. J. Org. Chem. 15 (1950) 1082
35. Finnegan W.G., Henry R.A., and Lofquist R. J. Am. Chem. Soc. 80 (1958) 3908
36. Ostrovskii V.A., Popilavskii V.S., Koldobskii G.I., and Erusalinkii G.B. Khim. Geterotsikl. Soedin. (1992) 1214
37. Koguro K., Oga T., Mitsui S., and Orita R. Synthesis (1998) 910
38. Demko Z.P., and Sharpless K.B. J. Org. Chem. 66 (2001) 7945
39. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem. Int. Ed. 40 (2001) 2004
40. Demko Z.P., and Sharpless K.B. Angew. Chem. Int. Ed. 41 (2002) 2110
41. Demko Z.P., and Sharpless K.B. Angew. Chem. Int. Ed. 41 (2002) 2113
42. van Leusen A.M., and Jagt J.C. Tetrahedron Lett. 12 (1970) 971
43. Jagt J.C., and van Leusen A.M. J. Org. Chem. 39 (1974) 564
44. Bayard P., Sainte R., and Ghosez L. Tetrahedron Lett. 29 (1988) 3799
45. Pews R.G., Nuqquist E.G., and Corson F.P. J. Org. Chem. 35 (1970) 4096
46. Janz J.T., and Monohan A.R. J. Org. Chem. 29 (1964) 569
47. Junge H., and Oehme G. Tetrahedron 54 (1998) 11027
48. Breitmaier E., and Rüffer U. Synthesis (1989) 623
49. Shi G.-Q., and Schlosser M. Tetrahedron 49 (1993) 1445
50. Hentemann M.F., Allen J.G., and Danishefsky S.J. Angew. Chem. Int. Ed. 39 (2000) 1937
51. Oppolzer W. Angew. Chem. Int. Ed. Engl. 11 (1972) 1031
52. Li W.-T., Lai F.-C., Lee G.-H., Pend S.-M., and Liu R.-S. J. Am. Chem. Soc. 120 (1998) 4520
53. Chen J., Song Q., Wang C., and Xi Z. J. Am. Chem. Soc. 124 (2002) 6238
54. Onsys'ko P.P., Sinitsa A., Pirozhenko V.V., and Chernega A.N. Heteroat. Chem. 13 (2002) 22
55. Korenchenko O.V., Aksinenko A.Y., Sokolov V.B., Pushin A.N., and Martynov I.V. Izv. Akad. Nauk Ser. Khim. (1995) 1809
56. Arnold Z., and Dvorak D. Coll. Czech. Chem. Commun. 50 (1985) 2265
57. Sulfonylcyanides have been used as electrophilic cyanation reagents. Christophersen C., Begrup M., Ebdrup S., Petersen H., and Vedsoe P. J. Org. Chem. 68 (2003) 9513
58. Boymond L., Rottlaender M., Cahiez G., and Knochel P. Angew. Chem. Int. Ed. Engl. 37 (1998) 1701
59. Jensen T., Teiler J., and Waernmark K. J. Org. Chem. 67 (2002) 6008
60. Wang T., and Hendrickson J. Org. Prep. Proced. Int. Ed. 35 (2003) 623
61. McClure C.K., and Link J.S. J. Org. Chem. 68 (2003) 8256
62. For a review of 1,3-bis(trimethylsilyloxy)-1,3-butadienes, see. Langer P. Synthesis (2002) 441
63. Preliminary communication:. Emmrich T., Reinke H., and Langer P. Synthesis (2006) 2551
64. Harfenist M., Joseph D.M., Spence S.C., Mcgee D.P.C., Reeves M.D., and White H.L. J. Med. Chem. 40 (1997) 2466
65. Colbry N.L., Elslager E.F., and Werbel L.M. J. Heterocycl. Chem. 21 (1984) 1521
66. Bristol J.A., Gold E.H., Lovey R.G., and Long J.F. J. Med. Chem. 24 (1981) 927
67. Bahuguna R.P., Joshi Y.C., Dobhal M.P., and Joshi B.C. Heterocycles 16 (1981) 1955
68. Bahuguna R.P. J. Indian Chem. Soc. 73 (1996) 618
69. Gangjee A., Zhu Y., and Queener S.F. J. Med. Chem. 41 (1998) 4533
70. Cutshall N.S., Ursino R., Kucera K.A., Latham J., and Ihle N.C. Bioorg. Med. Chem. Lett. 14 (2001) 1951
71. Anderson D.R., Hegde S., Reinhard E., Gomez L., Vernier W.F., Lee L., Liu S., Sambandam A., Snider P.A., and Masih L. Bioorg. Med. Chem. Lett. 15 (2005) 1587
72. Lu I.-L., Mahindroo N., Liang P.-H., Peng Y.-H., Kuo C.-J., Tsai K.-C., Hsieh H.-P., Chao Y.-S., and Wu S.-Y. J. Med. Chem. 49 (2006) 5154
73. Wilson K.J., van Niel M.B., Cooper L., Bloomfield D., O'Connor D., Fish L.R., and MacLeod A.M. Bioorg. Med. Chem. Lett. 17 (2007) 2643
74. Lavey B.J., Kozlowski J.A., Shankar B.B., Spitler J.M., Zhou G., Yang D.-Y., Shu Y., Wong M.K.C., Wong S.-C., Shih N.-Y., and Wu J. Bioorg. Med. Chem. Lett. 17 (2007) 3760
75. Hirokawa Y., Horikawa T., and Kato S. Chem. Pharm. Bull. 48 (2000) 1847
76. Furukawa N., Tsuruoka M., and Fujihara H. Heterocycles 24 (1986) 3337
77. Bonnet V., Mongin F., Trecourt F., Queguiner G., and Knochel P. Tetrahedron 58 (2002) 4429
78. Ohnmacht C.J., Russell K., Empfield J.R., Frank C.A., and Gibson K.H. J. Med. Chem. 39 (1996) 4592
79. Yogi S., Hokama K., and Tsuge O. Bull. Chem. Soc. Jpn. 60 (1987) 335
80. Reiffenrath V., and Bremer M. Angew. Chem. 106 (1994) 1435
81. Molander G.A., and Cameron K.O. J. Am. Chem. Soc. 115 (1993) 830
82. Anderson G., Cameron D.W., Feutrill G.I., and Read R.W. Tetrahedron Lett. 21 (1981) 4347
83. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-686724 (3l) and CCDC-686725 (3r). Copies of this data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk) or via www.ccdc.cam.ac.uk/conts/retrieving.html.