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Volumn , Issue 2, 2008, Pages 217-220

Iodoarene-mediated one-pot preparation of 2,4,5-trisubstituted oxazoles from ketones

Author keywords

2,4,5 trisubstituted oxazoles; Iodoarene; MCPBA; One pot reaction

Indexed keywords

2 ETHYL 4 HEPTYL 5 PHENYLOXAZOLE; 2 ETHYL 4 METHYL 5 PHENYLOXAZOLE; 2 ETHYL 5 (4' CHLOROPHENYL)OXAZOLE; 2 ETHYL 5 (4' METHYLPHENYL)OXAZOLE; 2 ETHYL 5 (4' NITROPHENYL)OXAZOLE; 2 ETHYL 5 PHENYLOXAZOLE; 2 ETHYLOXAZOLE DERIVATIVE; 2 METHYL 4 HEPTYL 5 PHENYL OXAZOLE; 2 METHYL 5 (4' CHLOROPHENYL)OXAZOLE; 2 METHYL 5 (4' METHYLPHENYL)OXAZOLE; 2 METHYL 5 (4' NITROPHENYL)OXAZOLE; 2 METHYL 5 PHENYLOXAZOLE; 2 METHYLOXAZOLE DERIVATIVE; 2,4 DIMETHYL 5 PHENYL OXAZOLE; 3 CHLOROPERBENZOIC ACID; ACETONITRILE; IODOARENE; KETONE; OXAZOLE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPIONITRILE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 38949182575     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1000871     Document Type: Article
Times cited : (26)

References (20)
  • 1
    • 38949189469 scopus 로고
    • Boyd, G. V, Katritzky, A. R, Rees, C. W, Eds, Pergamon: Oxford, Chap. 4.18
    • (a) Comprehensive Heterocyclic Chemistry, Vol. 6; Boyd, G. V.; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984, Chap. 4.18.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.6
  • 2
    • 38949132028 scopus 로고    scopus 로고
    • Hartner, F. W. J. r, Katritzky, A. R, Rees, C. W, Scriven, E. F. V, Eds, Elsevier Science: Oxford, Chap. 3.04
    • (b) Comprehensive Heterocyclic Chemistry II, Vol. 3; Hartner, F. W. J. r.; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier Science: Oxford, 1996, Chap. 3.04.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.3
  • 5
    • 0000314051 scopus 로고
    • (e) Wipf, P. Chem. Rev. 1995, 95, 2115.
    • (1995) Chem. Rev , vol.95 , pp. 2115
    • Wipf, P.1
  • 17
    • 38949172975 scopus 로고    scopus 로고
    • Typical Experimental Procedure: To a mixture of iodobenzene (purity 98, 1.1 mmol, 228 mg) and MCPBA (purity 65, 292 mg) in MeCN (8 mL) was added TfOH (2.0 mmol, 0.17 mL, The obtained mixture was stirred for 0.5 h at r.t. under an argon atmosphere. Then, a solution of acetophenone (purity 98.5, 1.0 mmol, 122 mg) in MeCN (2 mL) was added, and the mixture was stirred for 2 h under refluxing conditions. After the reaction, the reaction mixture was poured into sat. aq NaHCO3 solution and extracted with CHCl3 (3 x 30 mL, The organic layer was dried over Na2SO4. After filtration and removal of the solvent under reduced pressure, the residue was purified by preparative TLC on silica gel (eluent: hexane-EtOAc, 5:1) to give 2-methyl-5-phenyloxazole in 56% yield. 2-Methyl-5-phenyloxazole: mp 57-58.5°C (lit.12 mp 57-58°C, IR (KBr, 1580, 1560, 1480 cm-1. 1H NMR 400 MHz, CDCl3
    • 3): δ = 1.42 (t, J = 7.6 Hz, 3 H), 2.90 (q, J = 7.6 Hz, 2 H), 7.44 (s, 1 H), 7.76 (d, J = 9.0 Hz, 2 H), 8.28 (d, J = 9.0 Hz, 2 H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.