메뉴 건너뛰기




Volumn 8, Issue 24, 2006, Pages 5621-5624

Synthesis of 2-azaindolizines by using an iodine-mediated oxidative desulfurization promoted cyclization of N-2-pyridylmethyl thioamides and an investigation of their photophysical properties

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; INDOLIZINE DERIVATIVE; IODINE; METAL; PYRIDINE DERIVATIVE; SULFUR; THIOAMIDE;

EID: 33846011402     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0623623     Document Type: Article
Times cited : (123)

References (31)
  • 1
    • 33845994503 scopus 로고    scopus 로고
    • Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Black Science: Oxford, U.K., 2000; Chapter 25.
    • Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Black Science: Oxford, U.K., 2000; Chapter 25.
  • 2
    • 33846026110 scopus 로고    scopus 로고
    • Jpn. Kokai Tokkyo Koho JP 2001035664;, 170632
    • (a) Nakatsuka, M.; Shimamura, T. Jpn. Kokai Tokkyo Koho JP 2001035664; Chem. Abstr. 2001, 134, 170632.
    • (2001) Chem. Abstr , vol.134
    • Nakatsuka, M.1    Shimamura, T.2
  • 3
    • 33846024140 scopus 로고    scopus 로고
    • Jpn. Kokai Tokkyo Koho JP 2001006877;, 93136
    • (b) Tominaga, G.; Kohama, R.; Takano, A. Jpn. Kokai Tokkyo Koho JP 2001006877; Chem. Abstr. 2001, 134, 93136.
    • (2001) Chem. Abstr , vol.134
    • Tominaga, G.1    Kohama, R.2    Takano, A.3
  • 4
    • 33845993721 scopus 로고    scopus 로고
    • Jpn. Kokai Tokkyo Koho JP 2001057292;, 200276
    • (c) Kitazawa, D.; Tominaga, G.; Takano, A. Jpn. Kokai Tokkyo Koho JP 2001057292; Chem. Abstr. 2001, 134, 200276.
    • (2001) Chem. Abstr , vol.134
    • Kitazawa, D.1    Tominaga, G.2    Takano, A.3
  • 5
    • 33846029244 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 2005043630;, 440277
    • Nakamura, H.; Yamamoto, H. PCT Int. Appl. WO 2005043630; Chem. Abstr. 2005, 142, 440277.
    • (2005) Chem. Abstr , vol.142
    • Nakamura, H.1    Yamamoto, H.2
  • 6
    • 33846032776 scopus 로고    scopus 로고
    • Degoey, D. A.; Flentge, C. A.; Flosi, W. J.; Grampovnik, D. J.; Kempf, D. J.; Klein, L. L.; Yeung, M. C.; Randolph, J. T.; Wang, X. C.; Yu, S. U.S. Pat. Appl. Publ. U.S. 2005148623; Chem. Abstr. 2005, 143, 133693.
    • (a) Degoey, D. A.; Flentge, C. A.; Flosi, W. J.; Grampovnik, D. J.; Kempf, D. J.; Klein, L. L.; Yeung, M. C.; Randolph, J. T.; Wang, X. C.; Yu, S. U.S. Pat. Appl. Publ. U.S. 2005148623; Chem. Abstr. 2005, 143, 133693.
  • 8
    • 14944342193 scopus 로고    scopus 로고
    • See Supporting Information for full list of authors. (5) (a) Alcarazo, M.; Roseblade, S. J.; Cowley, A. R.; Fernández, R.; Brown, J. M.; Lassaletta, J. M. J. Am. Chem. Soc. 2005, 127, 3290.
    • See Supporting Information for full list of authors. (5) (a) Alcarazo, M.; Roseblade, S. J.; Cowley, A. R.; Fernández, R.; Brown, J. M.; Lassaletta, J. M. J. Am. Chem. Soc. 2005, 127, 3290.
  • 12
    • 0038547070 scopus 로고    scopus 로고
    • For recent advances in the synthesis of 2-azaindolizines via an acetic acid mediated condensation pathway, see: a
    • For recent advances in the synthesis of 2-azaindolizines via an acetic acid mediated condensation pathway, see: (a) Wang, J.; Mason, R.; VanDerveer, K.; Feng, D.; Bu, X. R. J. Org. Chem. 2003, 68, 5415.
    • (2003) J. Org. Chem , vol.68 , pp. 5415
    • Wang, J.1    Mason, R.2    VanDerveer, K.3    Feng, D.4    Bu, X.R.5
  • 14
    • 0037119337 scopus 로고    scopus 로고
    • For recent advances in the synthesis of 2-azaindolizines via an oxidative pathway, see: a
    • For recent advances in the synthesis of 2-azaindolizines via an oxidative pathway, see: (a) Bluhm, M. E.; Ciesielski, M.; Görls, H.; Döring, M. Angew. Chem., Int. Ed. 2002, 41, 2962.
    • (2002) Angew. Chem., Int. Ed , vol.41 , pp. 2962
    • Bluhm, M.E.1    Ciesielski, M.2    Görls, H.3    Döring, M.4
  • 16
    • 84876016119 scopus 로고    scopus 로고
    • Starting thioamides are readily prepared by the three-component Willgerodt-Kindler reaction of an aldehyde, amine, and elemental sulfur. See: Brown, E. V. Synthesis 1975, 358
    • Starting thioamides are readily prepared by the three-component Willgerodt-Kindler reaction of an aldehyde, amine, and elemental sulfur. See: Brown, E. V. Synthesis 1975, 358.
  • 17
    • 3242757492 scopus 로고    scopus 로고
    • For examples of our recent studies on thioamides, see: (a) Murai, T, Niwa, H, Kimura, T, Shibahara, F. Chem. Lett. 2004, 33, 508
    • For examples of our recent studies on thioamides, see: (a) Murai, T.; Niwa, H.; Kimura, T.; Shibahara, F. Chem. Lett. 2004, 33, 508.
  • 21
    • 37049140187 scopus 로고    scopus 로고
    • As only one example of compound 3, 3b, was reported, see: Glover, E. E.; Vaughan, K. D. J. Chem. Soc., Perkin Trans. 1 1973, 21, 2595.
    • As only one example of compound 3, 3b, was reported, see: Glover, E. E.; Vaughan, K. D. J. Chem. Soc., Perkin Trans. 1 1973, 21, 2595.
  • 22
    • 33846006326 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 23
    • 33846009911 scopus 로고    scopus 로고
    • 6 (in toluene under reflux for 4 h), but instead, insoluble material was precipitated.
    • 6 (in toluene under reflux for 4 h), but instead, insoluble material was precipitated.
  • 24
    • 0035805264 scopus 로고    scopus 로고
    • For related oxidative desulfurization reactions, such as (a) glycosidation via oxidative activation of a thioether, see
    • For related oxidative desulfurization reactions, such as (a) glycosidation via oxidative activation of a thioether, see: Nicolaou, K. C.; Mitchell, H. J. Angew. Chem., Int. Ed. 2001, 40, 1576.
    • (2001) Angew. Chem., Int. Ed , vol.40 , pp. 1576
    • Nicolaou, K.C.1    Mitchell, H.J.2
  • 26
    • 11844274689 scopus 로고    scopus 로고
    • Also see review: (c) Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214.
    • Also see review: (c) Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214.
  • 27
    • 33846009201 scopus 로고    scopus 로고
    • The reaction of 2-azaindolizine 2b and SCl2 provides 3b: see ref 11
    • 2 provides 3b: see ref 11.
  • 28
    • 12344337689 scopus 로고    scopus 로고
    • For a recent review of the Suzuki-Miyaura coupling reaction, see:, Int. Ed, and references cited therein
    • For a recent review of the Suzuki-Miyaura coupling reaction, see: Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366 and references cited therein.
    • (2005) Angew. Chem , vol.44 , pp. 366
    • Christmann, U.1    Vilar, R.2
  • 29
    • 33846010846 scopus 로고    scopus 로고
    • See Supporting Information for full detailed analytical data Table S1
    • See Supporting Information for full detailed analytical data (Table S1).
  • 31
    • 33845990891 scopus 로고    scopus 로고
    • See Supporting Information Figures S1 and S2
    • See Supporting Information (Figures S1 and S2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.