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Volumn , Issue 19, 2008, Pages 2945-2950

Aerial oxidation of 2,2-dibromo-1-aryl and heteroaryl ethanones: A facile synthesis of aryl and heteroaryl α-keto amides

Author keywords

keto amide; 2,2 dibromo 1 aryl and heteroaryl ethanone; Aerial oxidation; Oxygen; Secondary amine

Indexed keywords

2 OXOACID; 2,2 DIBROMO 1 ARYL; ALPHA KETO AMIDE DERIVATIVE; AMIDE; AMINE; DIBROMOETHANONE DERIVATIVE; HETEROARYL ETHANONE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 57649243424     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1087353     Document Type: Article
Times cited : (45)

References (64)
  • 25
    • 11744250899 scopus 로고
    • (a) Rau, H. Chem. Rev. 1983, 83, 535.
    • (1983) Chem. Rev , vol.83 , pp. 535
    • Rau, H.1
  • 26
  • 41
    • 0003779363 scopus 로고    scopus 로고
    • and 2; Beller, M, Bolm, C, Eds, Wiley-VCH: Weinheim
    • (b) Transition Metals for Organic Synthesis, Vol. 1 and 2; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998.
    • (1998) Transition Metals for Organic Synthesis , vol.1
  • 60
    • 57649168433 scopus 로고    scopus 로고
    • Representative Procedure for the Synthesis of 1-Phenyl-2-morpholin-1- yl-ethane-1,2-dione To a solution of 2,2-dibromo-1-phenylethanone (1a, 1 g, 0.0035 mol, 1 equiv) in THF (10 mL) was added morpholine (0.99 g, 0.014 mol, 4 equiv) dropwise over a period of 30 min at 20-30°C. The temperature of the reaction mixture was slowly raised to 40-50°C under an oxygen atmosphere and maintained for 18-26 h (monitored by TLC, After the completion of the reaction, THF was distilled off up to 80% of its The reaction mass was then diluted with CH2Cl2 (25 mL, washed with dil. HCl (10 mL, 4x, followed by brine. The organic layer was then dried over Na2SO4, and the product 2a was obtained after column chromatographic purification in 54% of yield as off-white solid; yield 57, IR (KBr, 1428, 1517, 1578, 1604, 1683, 1677, 2843 cm-1. 1H NMR (200 MHz, CDCl3, δ, 3.40 m, 2 H, 3.70
    • 3 (326.19): C, 51.55; H, 4.94; N, 4.29. Found: C, 51.53; H, 4.28; N, 4.83. 1-(3-Bromo-4-methoxy-phenyl)-2- pyrolidln-1-yl-ethane-1,2-dfone (2h) Yield 57%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.