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Synlett
Volumn , Issue 8, 2008, Pages 1145-1148
A new simple route to the thieno[2,3-b]indole ring system
Author keywords

Furan; Fused ring system; Ring closure; Ring opening; Thieno 2,3 b indole
Indexed keywords

FURAN DERIVATIVE; THIENO[2,3 B]INDOLE;
EID: 44349085288     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072720     Document Type: Article
Times cited : (32)
References (46)
  • 2
    • 28444442820 scopus 로고
    • Chem. Abstr. 1969, 70, 96665.
    • (1969) Chem. Abstr , vol.70 , pp. 96665
  • 40
    • 44349185887 scopus 로고    scopus 로고
    • Compounds 3 were prepared using the Meerwein method. For a typical procedure, see ref. 16b. General Procedure for the Arylation Reaction A mixture of substituted 2-nitroaniline (0.3 mol, H2O (400 mL) and 36% HCl (200 mL) was stirred for 30 min at 80°C. The solution was then cooled to 0°C to -10°C. The resulting suspension of aniline hydrochloride was treated with NaNO2 (25 g, 0.36 mol) in H 2O (120 mL, The resulting solution of the diazonium salt was stirred for 40 min at 0°C to -5°C and filtered. A solution of furfural or 2-acetylfuran (0.3 mol) in acetone (150 mL) was added, followed by CuCl 2 (8 g, 0.06 mol) in H2O (100 mL, The reaction mixture was stirred for 12 h at r.t. When the reaction was complete, the resulting precipitate was filtered off and crystallized from EtOH-acetone; yields of 5-arylfurfurals 3a,c-e: 45-53, yield of 2-acetyl-5-phenylfuran 3b, 41
    • 2O (100 mL). The reaction mixture was stirred for 12 h at r.t. When the reaction was complete, the resulting precipitate was filtered off and crystallized from EtOH-acetone; yields of 5-arylfurfurals 3a,c-e: 45-53%; yield of 2-acetyl-5-phenylfuran (3b): 41%.
  • 42
    • 44349091267 scopus 로고    scopus 로고
    • Compounds 4 were synthesized according to the reported procedure, see ref. 17b. General Procedure for the Preparation of Compounds 4a-e To a cooled (0-5°C) solution of compound 3 (17 mmol) in THF (120 mL, anhyd AlCl3 (4.5 g, 34 mmol) and NaBH4 (1.3 g, 34 mmol) were added portionwise under stirring. The resulting suspension was stirred at 0-5°C for 20 min and then brought to reflux. After 1-2 h when the starting compound 3 vanished (TLC monitoring, the reaction mixture was cooled and poured into H2O (400 mL, The organic layer was separated and the water layer was extracted with EtOAc (3 x 50 mL, The combined organic layers were dried over anhyd Na2SO4, treated with activated charcoal, and the solvent evaporated under the reduced pressure. The residue 4 was used in the next step without further purification, b) Ono, A, Suzuki, N, Kamimura, J. Synthesis 1987, 736
    • 4, treated with activated charcoal, and the solvent evaporated under the reduced pressure. The residue 4 was used in the next step without further purification. (b) Ono, A.; Suzuki, N.; Kamimura, J. Synthesis 1987, 736.
  • 43
    • 44349110464 scopus 로고    scopus 로고
    • General Procedure for the Preparation of Compounds 5a-e To an ethanolic solution (50 mL) of compound 4 (6 mmol), Raney Ni (1.5 g) and hydrazine hydrate (2.5 mL) were added and the reaction mixture was refluxed for 1-2 h. After completion of the reaction (TLC monitoring), the catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was dissolved in benzene-PE (1:1), filtered through a pad of silica gel, and the solvent evaporated under reduced pressure. The residue 5 was used in the next step without further purification. WARNING: Care should be taken when handling benzene as a solvent due to its carcinogenic properties.
    • General Procedure for the Preparation of Compounds 5a-e To an ethanolic solution (50 mL) of compound 4 (6 mmol), Raney Ni (1.5 g) and hydrazine hydrate (2.5 mL) were added and the reaction mixture was refluxed for 1-2 h. After completion of the reaction (TLC monitoring), the catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was dissolved in benzene-PE (1:1), filtered through a pad of silica gel, and the solvent evaporated under reduced pressure. The residue 5 was used in the next step without further purification. WARNING: Care should be taken when handling benzene as a solvent due to its carcinogenic properties.
  • 44
    • 44349156841 scopus 로고    scopus 로고
    • General Procedure for the Preparation of Compounds 6a-e A solution of thiophosgene (0.5 mL, 6.5 mmol) in CH2Cl2 (10 mL) and NaHCO3 (1.3 g, 15.5 mmol) in H2O (50 mL) were simultaneously added at r.t. to a stirred solution of compound 5 (5 mmol) in CH2Cl2 (15 mL, When the reaction had finished (TLC monitoring, the mixture was poured into H2O (200 mL) and stirred for 6 h. The organic layer was separated and water layer was extracted with CH 2Cl2 2 x 50 mL, The combined organic layers were dried over anhyd Na2SO4, the dried extract was reduced to the half of its and PE was added until the solution became cloudy. The solution was filtered through a pad of silica gel, evaporated to one third of its and left to allow crystallization of the compounds 6. Selected Analytical Data of 6e Mp 85-86°C IR: νmax, 2136, 1616
    • 2S: C, 63.65; H, 4.52; N, 5.71. Found: C, 63.86; H, 4.38; N, 5.79.
  • 45
    • 44349131282 scopus 로고    scopus 로고
    • General Procedure for the Preparation of Compounds 8a-e Aluminum chloride (1.6 g, 12 mmol) was added to a solution of compound 6 (6 mmol) in 1,2-dichloroethane (30 mL, The reaction mixture was stirred for 30 min at 50°C (TLC monitoring, then poured into H2O (200 mL) and extracted with CH2Cl2 (2 x 40 mL, The combined extracts were dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was crystallized from the appropriate solvent: benzene-PE for 8a; benzene for 8b; EtOH for 8c; EtOAc-PE for 8d; EtOH for 8e. WARNING: Care should be taken when handling benzene as a solvent because of its carcinogenic properties. Selected Analytical Data of 8e Mp 225-226°C IR: νmax, 1628, 1608, 1584, 1508, 1480, 1472, 1400, 1280, 1236, 1196, 1156, 1092, 1024, 936, 824, 808 cm-1. 1H NMR 300 MHz, CDCl3, δ
    • 2S: C, 63.65; H, 4.52; N, 5.71. Found: C, 63.69; H, 4.41; N, 5.77.
  • 46
    • 44349150757 scopus 로고    scopus 로고
    • Crystal Data of Compound 8a C12H9NOS, orthorhombic, space group Pbca; a, 11.982(2) Å, b, 10.837(2) Å, c, 15.752(3) Å, V, 2045.4(6) Å3, Z, 8, Dcalcd, 1.398 Mg/m 3, F(000, 896; 1797 reflections collected, 1797 unique (Rint, 0.0000, final R indices (935 observed collections I > 2σI, R1, 0.0309, wR2, 0.0924; final R indices (all data, R 1, 0.0859, wR2, 0.1005. Crystallographic data (excluding structure factors) for the structure in this article have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 657300. Copies of the 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@c
    • 2 = 0.1005. Crystallographic data (excluding structure factors) for the structure in this article have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 657300. Copies of the 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.uc]. Each request should be accompanied by the complete citation of this paper.

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