메뉴 건너뛰기




Volumn 7, Issue 5, 2005, Pages 791-794

Synthesis of thienothiopyranthiones by a new molecular rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DITHIOLE DERIVATIVE; 4H THIENO[2,3 C]THIOPYRAN 7 THIONE; 7H THIENO[2,3 C]THIOPYRAN 7 THIONE; ALKYNE DERIVATIVE; CHLORINE; THIOPHENE DERIVATIVE; THIOPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 15044358043     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0476669     Document Type: Article
Times cited : (25)

References (30)
  • 1
    • 0037276683 scopus 로고    scopus 로고
    • Sudakin, D. L. J. Toxicol., Clin. Toxicol. 2003, 41, 195. Navamal, M.; McGrath, C.; Stewart, J.; Blans, P.; Villamena, F.; Zweier J.; Fishbein, J. C. J. Org. Chem. 2002, 67, 9406 and refs cited therein. Barriga, S.; Fuertes, P.; Marcos C. F.; Torroba, T. J. Org. Chem. 2004, 69, 3672 and refs cited therein.
    • (2003) J. Toxicol., Clin. Toxicol. , vol.41 , pp. 195
    • Sudakin, D.L.1
  • 2
    • 0037184764 scopus 로고    scopus 로고
    • and refs cited therein
    • Sudakin, D. L. J. Toxicol., Clin. Toxicol. 2003, 41, 195. Navamal, M.; McGrath, C.; Stewart, J.; Blans, P.; Villamena, F.; Zweier J.; Fishbein, J. C. J. Org. Chem. 2002, 67, 9406 and refs cited therein. Barriga, S.; Fuertes, P.; Marcos C. F.; Torroba, T. J. Org. Chem. 2004, 69, 3672 and refs cited therein.
    • (2002) J. Org. Chem. , vol.67 , pp. 9406
    • Navamal, M.1    McGrath, C.2    Stewart, J.3    Blans, P.4    Villamena, F.5    Zweier, J.6    Fishbein, J.C.7
  • 3
    • 2442662862 scopus 로고    scopus 로고
    • and refs cited therein
    • Sudakin, D. L. J. Toxicol., Clin. Toxicol. 2003, 41, 195. Navamal, M.; McGrath, C.; Stewart, J.; Blans, P.; Villamena, F.; Zweier J.; Fishbein, J. C. J. Org. Chem. 2002, 67, 9406 and refs cited therein. Barriga, S.; Fuertes, P.; Marcos C. F.; Torroba, T. J. Org. Chem. 2004, 69, 3672 and refs cited therein.
    • (2004) J. Org. Chem. , vol.69 , pp. 3672
    • Barriga, S.1    Fuertes, P.2    Marcos, C.F.3    Torroba, T.4
  • 4
    • 0038683154 scopus 로고    scopus 로고
    • Yao, K.-S.; O'Dwyer, P. J. Biochem. Pharmacol. 2003, 66, 15. Miao, W.; Hu, L.; Kandouz, M.; Batist, G. Mol. Pharmacol. 2003, 64, 346. (3) Kwak, M.-K.; Wakabayashi, N.; Itoh, K.; Motohashi, H.; Yamamoto, M.; Kensler, T. W. J. Biol. Chem. 2003, 278, 8135.
    • (2003) Biochem. Pharmacol. , vol.66 , pp. 15
    • Yao, K.-S.1    O'Dwyer, P.J.2
  • 5
    • 0041341933 scopus 로고    scopus 로고
    • Yao, K.-S.; O'Dwyer, P. J. Biochem. Pharmacol. 2003, 66, 15. Miao, W.; Hu, L.; Kandouz, M.; Batist, G. Mol. Pharmacol. 2003, 64, 346. (3) Kwak, M.-K.; Wakabayashi, N.; Itoh, K.; Motohashi, H.; Yamamoto, M.; Kensler, T. W. J. Biol. Chem. 2003, 278, 8135.
    • (2003) Mol. Pharmacol. , vol.64 , pp. 346
    • Miao, W.1    Hu, L.2    Kandouz, M.3    Batist, G.4
  • 8
    • 0000176221 scopus 로고
    • Pedersen, C. Th. Adv. Heterocycl. Chem. 1982, 31, 63. Pedersen, C. Th. Sulfur Rep. 1995, 16, 173.
    • (1995) Sulfur Rep. , vol.16 , pp. 173
    • Pedersen, C.Th.1
  • 9
  • 10
    • 0001360366 scopus 로고
    • McKinnon, D. M.; Secco A. S.; Duncan, K. A. Can. J. Chem. 1987, 65, 1247. Fanghanel, E.; Palmer, T.; Kersten, J.; Ludwigs, R.; Peters, K.; von Schnering, H. G. Synthesis 1994, 1067. Marcos, C. E.; Polo, C.; Rakitin, O. A.; Rees, C. W.; Torroba, T. Chem. Commun. 1997, 879
    • (1987) Can. J. Chem. , vol.65 , pp. 1247
    • McKinnon, D.M.1    Secco, A.S.2    Duncan, K.A.3
  • 12
    • 0001457275 scopus 로고    scopus 로고
    • McKinnon, D. M.; Secco A. S.; Duncan, K. A. Can. J. Chem. 1987, 65, 1247. Fanghanel, E.; Palmer, T.; Kersten, J.; Ludwigs, R.; Peters, K.; von Schnering, H. G. Synthesis 1994, 1067. Marcos, C. E.; Polo, C.; Rakitin, O. A.; Rees, C. W.; Torroba, T. Chem. Commun. 1997, 879
    • (1997) Chem. Commun. , pp. 879
    • Marcos, C.E.1    Polo, C.2    Rakitin, O.A.3    Rees, C.W.4    Torroba, T.5
  • 15
    • 15044350923 scopus 로고    scopus 로고
    • note
    • X-ray data for 3a, 4aa, 5bb, 5bc, and 5cb have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 255373-255377 and are also available in Supporting Information.
  • 17
    • 15044365322 scopus 로고
    • Brandsma, L.; Bos, H. J. Recl. Trav. Chim. 1969, 88, 732. Young, T. E.; Hamel, C. R. J. Org. Chem. 1970, 35, 816 and 821. Schuijl-Laros, D.; Schuijl, P. J. W.; Brandsma, L. Recl. Trav. Chim. 1972, 91, 785. Alam, I.; Thyagarajan, G. Tetrahedron 1973, 29, 1829. Grafing, R.; Brandsma, L. Synthesis 1978, 578. Grafing, R.; Brandsma, L. Recl. Trav. Chim. 1980, 99, 23. Ramadas S. R.; Chandrakumar, N. S. Phosphorus Sulfur 1982, 13, 79. Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941 . Marchand, E.; Morel, G. Bull. Soc. Chim. Fr. 1996, 133, 903. Mandal, S. S.; Chakraborty, J. J. Chem. Soc., Perkin Trans. 1 1999, 2639.
    • (1969) Recl. Trav. Chim. , vol.88 , pp. 732
    • Brandsma, L.1    Bos, H.J.2
  • 18
    • 15044358873 scopus 로고
    • Brandsma, L.; Bos, H. J. Recl. Trav. Chim. 1969, 88, 732. Young, T. E.; Hamel, C. R. J. Org. Chem. 1970, 35, 816 and 821. Schuijl-Laros, D.; Schuijl, P. J. W.; Brandsma, L. Recl. Trav. Chim. 1972, 91, 785. Alam, I.; Thyagarajan, G. Tetrahedron 1973, 29, 1829. Grafing, R.; Brandsma, L. Synthesis 1978, 578. Grafing, R.; Brandsma, L. Recl. Trav. Chim. 1980, 99, 23. Ramadas S. R.; Chandrakumar, N. S. Phosphorus Sulfur 1982, 13, 79. Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941 . Marchand, E.; Morel, G. Bull. Soc. Chim. Fr. 1996, 133, 903. Mandal, S. S.; Chakraborty, J. J. Chem. Soc., Perkin Trans. 1 1999, 2639.
    • (1970) J. Org. Chem. , vol.35 , pp. 816
    • Young, T.E.1    Hamel, C.R.2
  • 19
    • 84943077617 scopus 로고
    • Brandsma, L.; Bos, H. J. Recl. Trav. Chim. 1969, 88, 732. Young, T. E.; Hamel, C. R. J. Org. Chem. 1970, 35, 816 and 821. Schuijl-Laros, D.; Schuijl, P. J. W.; Brandsma, L. Recl. Trav. Chim. 1972, 91, 785. Alam, I.; Thyagarajan, G. Tetrahedron 1973, 29, 1829. Grafing, R.; Brandsma, L. Synthesis 1978, 578. Grafing, R.; Brandsma, L. Recl. Trav. Chim. 1980, 99, 23. Ramadas S. R.; Chandrakumar, N. S. Phosphorus Sulfur 1982, 13, 79. Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941 . Marchand, E.; Morel, G. Bull. Soc. Chim. Fr. 1996, 133, 903. Mandal, S. S.; Chakraborty, J. J. Chem. Soc., Perkin Trans. 1 1999, 2639.
    • (1972) Recl. Trav. Chim. , vol.91 , pp. 785
    • Schuijl-Laros, D.1    Schuijl, P.J.W.2    Brandsma, L.3
  • 20
    • 15044361015 scopus 로고
    • Brandsma, L.; Bos, H. J. Recl. Trav. Chim. 1969, 88, 732. Young, T. E.; Hamel, C. R. J. Org. Chem. 1970, 35, 816 and 821. Schuijl-Laros, D.; Schuijl, P. J. W.; Brandsma, L. Recl. Trav. Chim. 1972, 91, 785. Alam, I.; Thyagarajan, G. Tetrahedron 1973, 29, 1829. Grafing, R.; Brandsma, L. Synthesis 1978, 578. Grafing, R.; Brandsma, L. Recl. Trav. Chim. 1980, 99, 23. Ramadas S. R.; Chandrakumar, N. S. Phosphorus Sulfur 1982, 13, 79. Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941 . Marchand, E.; Morel, G. Bull. Soc. Chim. Fr. 1996, 133, 903. Mandal, S. S.; Chakraborty, J. J. Chem. Soc., Perkin Trans. 1 1999, 2639.
    • (1973) Tetrahedron , vol.29 , pp. 1829
    • Alam, I.1    Thyagarajan, G.2
  • 21
    • 85065822306 scopus 로고
    • Brandsma, L.; Bos, H. J. Recl. Trav. Chim. 1969, 88, 732. Young, T. E.; Hamel, C. R. J. Org. Chem. 1970, 35, 816 and 821. Schuijl-Laros, D.; Schuijl, P. J. W.; Brandsma, L. Recl. Trav. Chim. 1972, 91, 785. Alam, I.; Thyagarajan, G. Tetrahedron 1973, 29, 1829. Grafing, R.; Brandsma, L. Synthesis 1978, 578. Grafing, R.; Brandsma, L. Recl. Trav. Chim. 1980, 99, 23. Ramadas S. R.; Chandrakumar, N. S. Phosphorus Sulfur 1982, 13, 79. Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941 . Marchand, E.; Morel, G. Bull. Soc. Chim. Fr. 1996, 133, 903. Mandal, S. S.; Chakraborty, J. J. Chem. Soc., Perkin Trans. 1 1999, 2639.
    • (1978) Synthesis , pp. 578
    • Grafing, R.1    Brandsma, L.2
  • 22
    • 70350477315 scopus 로고
    • Brandsma, L.; Bos, H. J. Recl. Trav. Chim. 1969, 88, 732. Young, T. E.; Hamel, C. R. J. Org. Chem. 1970, 35, 816 and 821. Schuijl-Laros, D.; Schuijl, P. J. W.; Brandsma, L. Recl. Trav. Chim. 1972, 91, 785. Alam, I.; Thyagarajan, G. Tetrahedron 1973, 29, 1829. Grafing, R.; Brandsma, L. Synthesis 1978, 578. Grafing, R.; Brandsma, L. Recl. Trav. Chim. 1980, 99, 23. Ramadas S. R.; Chandrakumar, N. S. Phosphorus Sulfur 1982, 13, 79. Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941 . Marchand, E.; Morel, G. Bull. Soc. Chim. Fr. 1996, 133, 903. Mandal, S. S.; Chakraborty, J. J. Chem. Soc., Perkin Trans. 1 1999, 2639.
    • (1980) Recl. Trav. Chim. , vol.99 , pp. 23
    • Grafing, R.1    Brandsma, L.2
  • 23
    • 15044346975 scopus 로고
    • Brandsma, L.; Bos, H. J. Recl. Trav. Chim. 1969, 88, 732. Young, T. E.; Hamel, C. R. J. Org. Chem. 1970, 35, 816 and 821. Schuijl-Laros, D.; Schuijl, P. J. W.; Brandsma, L. Recl. Trav. Chim. 1972, 91, 785. Alam, I.; Thyagarajan, G. Tetrahedron 1973, 29, 1829. Grafing, R.; Brandsma, L. Synthesis 1978, 578. Grafing, R.; Brandsma, L. Recl. Trav. Chim. 1980, 99, 23. Ramadas S. R.; Chandrakumar, N. S. Phosphorus Sulfur 1982, 13, 79. Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941 . Marchand, E.; Morel, G. Bull. Soc. Chim. Fr. 1996, 133, 903. Mandal, S. S.; Chakraborty, J. J. Chem. Soc., Perkin Trans. 1 1999, 2639.
    • (1982) Phosphorus Sulfur , vol.13 , pp. 79
    • Ramadas, S.R.1    Chandrakumar, N.S.2
  • 24
    • 0000969806 scopus 로고
    • Brandsma, L.; Bos, H. J. Recl. Trav. Chim. 1969, 88, 732. Young, T. E.; Hamel, C. R. J. Org. Chem. 1970, 35, 816 and 821. Schuijl-Laros, D.; Schuijl, P. J. W.; Brandsma, L. Recl. Trav. Chim. 1972, 91, 785. Alam, I.; Thyagarajan, G. Tetrahedron 1973, 29, 1829. Grafing, R.; Brandsma, L. Synthesis 1978, 578. Grafing, R.; Brandsma, L. Recl. Trav. Chim. 1980, 99, 23. Ramadas S. R.; Chandrakumar, N. S. Phosphorus Sulfur 1982, 13, 79. Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941 . Marchand, E.; Morel, G. Bull. Soc. Chim. Fr. 1996, 133, 903. Mandal, S. S.; Chakraborty, J. J. Chem. Soc., Perkin Trans. 1 1999, 2639.
    • (1995) J. Org. Chem. , vol.60 , pp. 7941
    • Benati, L.1    Capella, L.2    Montevecchi, P.C.3    Spagnolo, P.4
  • 25
    • 0000283688 scopus 로고    scopus 로고
    • Brandsma, L.; Bos, H. J. Recl. Trav. Chim. 1969, 88, 732. Young, T. E.; Hamel, C. R. J. Org. Chem. 1970, 35, 816 and 821. Schuijl-Laros, D.; Schuijl, P. J. W.; Brandsma, L. Recl. Trav. Chim. 1972, 91, 785. Alam, I.; Thyagarajan, G. Tetrahedron 1973, 29, 1829. Grafing, R.; Brandsma, L. Synthesis 1978, 578. Grafing, R.; Brandsma, L. Recl. Trav. Chim. 1980, 99, 23. Ramadas S. R.; Chandrakumar, N. S. Phosphorus Sulfur 1982, 13, 79. Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941 . Marchand, E.; Morel, G. Bull. Soc. Chim. Fr. 1996, 133, 903. Mandal, S. S.; Chakraborty, J. J. Chem. Soc., Perkin Trans. 1 1999, 2639.
    • (1996) Bull. Soc. Chim. Fr. , vol.133 , pp. 903
    • Marchand, E.1    Morel, G.2
  • 26
    • 15044362664 scopus 로고    scopus 로고
    • Brandsma, L.; Bos, H. J. Recl. Trav. Chim. 1969, 88, 732. Young, T. E.; Hamel, C. R. J. Org. Chem. 1970, 35, 816 and 821. Schuijl-Laros, D.; Schuijl, P. J. W.; Brandsma, L. Recl. Trav. Chim. 1972, 91, 785. Alam, I.; Thyagarajan, G. Tetrahedron 1973, 29, 1829. Grafing, R.; Brandsma, L. Synthesis 1978, 578. Grafing, R.; Brandsma, L. Recl. Trav. Chim. 1980, 99, 23. Ramadas S. R.; Chandrakumar, N. S. Phosphorus Sulfur 1982, 13, 79. Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941 . Marchand, E.; Morel, G. Bull. Soc. Chim. Fr. 1996, 133, 903. Mandal, S. S.; Chakraborty, J. J. Chem. Soc., Perkin Trans. 1 1999, 2639.
    • (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 2639
    • Mandal, S.S.1    Chakraborty, J.2
  • 27
    • 4243553426 scopus 로고
    • Becke, A. D. Phys. Rev. A 1988, 38, 3098; Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
    • (1988) Phys. Rev. A , vol.38 , pp. 3098
    • Becke, A.D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.