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Organic Letters
Volumn 9, Issue 26, 2007, Pages 5573-5576
Synthesis of benzo[b]thiophenes by cyclization of arylketene dithioacetal monoxides under pummerer-like conditions
Author keywords

[No Author keywords available]
Indexed keywords

ACETAL DERIVATIVE; BENZOTHIOPHENE; THIOPHENE DERIVATIVE;
EID: 38349166185     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702643j     Document Type: Article
Times cited : (72)
References (36)
  • 1
    • 0024377629 scopus 로고    scopus 로고
    • Selected examples: (a) Graham, S. L.; Shepard, K. L.; Anderson, P. S.; Baldwin, J. J.; Best, D. B.; Christy, M. E.; Freedman, M. B.; Gautheron, P.; Habecker, C. N.; Hoffman, J. M.; Lyle, P. A.; Michelson, S. R.; Ponticello, G. S.; Robb, C. M.; Schwam, H.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Strohmaier, K. M.; Sugrue, M. F.; Varga, S. L. J. Med. Chem. 1989, 32, 2548-2554.
    • Selected examples: (a) Graham, S. L.; Shepard, K. L.; Anderson, P. S.; Baldwin, J. J.; Best, D. B.; Christy, M. E.; Freedman, M. B.; Gautheron, P.; Habecker, C. N.; Hoffman, J. M.; Lyle, P. A.; Michelson, S. R.; Ponticello, G. S.; Robb, C. M.; Schwam, H.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Strohmaier, K. M.; Sugrue, M. F.; Varga, S. L. J. Med. Chem. 1989, 32, 2548-2554.
  • 4
    • 0344737904 scopus 로고    scopus 로고
    • Selected examples: (a) Kim, M.-S.; Maruyama, H.; Kawai, T.; Irie, M. Chem. Mater. 2003, 15, 4539-4543.
    • Selected examples: (a) Kim, M.-S.; Maruyama, H.; Kawai, T.; Irie, M. Chem. Mater. 2003, 15, 4539-4543.
  • 9
    • 0348080703 scopus 로고    scopus 로고
    • (f) Irie, M. Chem. Rev. 2000, 100, 1685-1716.
    • (2000) Chem. Rev , vol.100 , pp. 1685-1716
    • Irie, M.1
  • 11
    • 33746309818 scopus 로고    scopus 로고
    • Selected recent examples: (a) Nakamura, I.; Sato, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 4473-4475.
    • Selected recent examples: (a) Nakamura, I.; Sato, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 4473-4475.
  • 20
    • 38349091863 scopus 로고    scopus 로고
    • Experimental procedure: Formaldehyde dimethyl dithioacetal S-oxide (1.0 mL, 10 mmol) and THF (10 mL) were placed in a flask under an atmosphere of argon. n-Butyllithium in hexane (1.62 M, 6.0 mL, 10 mmol) was added to the solution at -20°C, and the mixture was stirred at the same temperature for 30 min. Benzophenone (2.2 g, 12 mmol) was added to the reaction mixture, and the mixture was stirred at -20°C for 6 h. Acetic anhydride (1.0 mL, 11 mmol) was added to the reaction mixture, and the mixture was stirred at -20°C for 12 h. Saturated aqueous NH4Cl was poured into the mixture, and the product was extracted with ethyl acetate (20 mL × 3, The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude mixture, benzene (10 mL, and tert-butyl alcohol (10 mL) were placed in a flask under an atmosphere of argon. Potassium tert-butoxide was added to the solution at 25°C, and the mixture was stirr
    • 4 and concentrated in vacuo. Purification by chromatography on silica gel provided methyl 1-methylsulfinyl-2,2-diphenylethenyl sulfide (1a, 1.84g, 66%).
  • 21
    • 38349103546 scopus 로고    scopus 로고
    • Experimental procedure: Methyl 1-methylsulfinyl-2,2- diphenylethenyl sulfide (1a, 54.9 mg, 0.19 mmol, K2CO3 (90.4 mg, 0.66 mmol, and toluene (4.0 mL) were placed in a flask under an atmosphere of argon. Trifluoromethanesulfonic anhydride (0.045 mL, 0.27 mmol) was added, and the mixture was stirred at 25°C for 1 h. Ethanolamine (0.060 mL, 1.0 mmol) was added to the reaction mixture, and the mixture was stirred at 25°C for 3 h. Saturated aqueous NaHCO3 was poured into the mixture and the product was extracted with ethyl acetate (3 × 20 mL, The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by chromatography on silica gel provided 2-methylthio-3-phenylbenzo[b]thiophene 5a, 42.2 mg, 0.16 mmol, 86
    • 4 and concentrated in vacuo. Purification by chromatography on silica gel provided 2-methylthio-3-phenylbenzo[b]thiophene (5a, 42.2 mg, 0.16 mmol, 86%).
  • 27
    • 0034640532 scopus 로고    scopus 로고
    • 2O and its applications were summarized: Baraznenok, I. L.; Nenajdenko. V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077-3119.
    • 2O and its applications were summarized: Baraznenok, I. L.; Nenajdenko. V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077-3119.
  • 28
    • 38349164308 scopus 로고    scopus 로고
    • The biological activity of 3-trifluoromethylbenzo[b]thiophene has been attracting attention
    • The biological activity of 3-trifluoromethylbenzo[b]thiophene has been attracting attention.
  • 32
    • 45149140245 scopus 로고    scopus 로고
    • Synthesis of 3-trifluoromethylbenzo[b]thiophenes is not easy. (a) Sawada, H.; Nakayama, M.; Yoshida, M.; Yoshida, T.; Kamigata, N. J. Fluorine Chem. 1990, 46, 423-431.
    • Synthesis of 3-trifluoromethylbenzo[b]thiophenes is not easy. (a) Sawada, H.; Nakayama, M.; Yoshida, M.; Yoshida, T.; Kamigata, N. J. Fluorine Chem. 1990, 46, 423-431.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.