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Volumn , Issue 3, 2007, Pages 465-469

New benzothiazole and benzoxazole scaffolds from the Ugi-Smiles couplings of heterocyclic thiols

Author keywords

Benzothiazole; Benzoxazole; Multicomponent reaction; Thioamides

Indexed keywords

2 MERCAPTOBENZOTHIAZOLE; 2 MERCAPTOBENZOXAZOLE; ALDEHYDE DERIVATIVE; AMINE; BENZOTHIAZOLE; BENZOXAZOLE DERIVATIVE; CYANIDE; HETEROCYCLIC COMPOUND; ISOCYANIDE DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33847362709     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-968027     Document Type: Article
Times cited : (23)

References (36)
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    • SO2 leaving group
    • 2 leaving group: (a) Hoggarth, E. J. Chem. Soc. 1949, 3311.
    • (1949) J. Chem. Soc , pp. 3311
  • 16
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    • Cl leaving group: (c) Advani, S. P.; Sam, J. J. Pharm. Sci. 1968, 57, 1693.
    • Cl leaving group: (c) Advani, S. P.; Sam, J. J. Pharm. Sci. 1968, 57, 1693.
  • 26
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    • See ref. 5b
    • (d) See ref. 5b.
  • 27
    • 33847382334 scopus 로고    scopus 로고
    • Preparation of Thioamide 4b; Typical Procedure To a 1 M solution of carbonyl compound 1b in toluene were added the amine 2a (1.0 equiv, the isocyanide 3a (1.0 equiv)and the mercapto benzoxazole (1.0 equiv, The resulting mixture was stirred at 50°C under an inert atmosphere for 2 d and concentrated in vacuo. The crude product was then purified by flash chromatography on silica gel to give the desired adduct 4b. 1H NMR (400 MHz, CDCl3, δ, 10.00 (br s, 1 H, 7.38-7.28 (m, 6 H, 7.24 (td, 1 H, J, 7.8, 1.3 Hz, 7.12 (td, 1 H, J, 7.8, 1.3 Hz, 4.96 (d, 1 H, J, 16.2 Hz, 4.76 (d, 1 H, J, 16.2 Hz, 4.53 (t, 1 H, J, 7.6 Hz, 2.36-2.24 (m, 1 H, 2.12-2.02 (m, 1 H, 1.52 (s, 9 H, 0.82 (t, 3 H, J, 7.3 Hz, 13C NMR 100.6 MHz, CDCl 3, δ, 199.2, 162.8, 148.9, 142.3, 136.5, 133.9, 129.7, 129.1, 124.8, 121.8, 116.5, 109.7, 74.1, 56.0, 51.7, 27.5, 24.2, 1
    • 3OS: 415.1485; found: 415.1471.
  • 28
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    • Oxazoles and their Benzo Derivatives
    • Katrizky, A. R, Ed, Pergamon: Oxford
    • (a) Boyd, G. V. Oxazoles and their Benzo Derivatives, In Comprehensive Heterocyclic Chemistry, Vol. 6; Katrizky, A. R., Ed.; Pergamon: Oxford, 1997, 178-233.
    • (1997) Comprehensive Heterocyclic Chemistry , vol.6 , pp. 178-233
    • Boyd, G.V.1
  • 29
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    • Thiazoles and their Benzo Derivatives
    • Katrizky, A. R, Ed, Pergamon: Oxford
    • (b) Metzger, J. V. Thiazoles and their Benzo Derivatives, In Comprehensive Heterocyclic Chemistry, Vol. 6; Katrizky, A. R., Ed.; Pergamon: Oxford, 1997, 236-330.
    • (1997) Comprehensive Heterocyclic Chemistry , vol.6 , pp. 236-330
    • Metzger, J.V.1
  • 30
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    • For general reviews on Ugi-based multicomponent reactions, see: a
    • For general reviews on Ugi-based multicomponent reactions, see: (a) Banfi, L.; Riva, R. Org. React. 2005, 65, 1.
    • (2005) Org. React , vol.65 , pp. 1
    • Banfi, L.1    Riva, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.