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Synlett
Volumn , Issue 9, 2007, Pages 1403-1406
Novel one-pot synthesis of N-alkyl arylamines from oxime ethers using organometallic reagents
Author keywords

Arylamine; Grignard reagent; One pot synthesis; Organolithium reagent; Oxime ether; Rearrangement
Indexed keywords

AROMATIC AMINE; HEXANE; N (DIALLYL)METHYL ARYLAMINE DERIVATIVE; N ALKYL ARYLAMINE DERIVATIVE; ORGANOLITHIUM COMPOUND; ORGANOMETALLIC COMPOUND; OXIME DERIVATIVE; REAGENT; TETRAHYDROFURAN; TOLUENE; UNCLASSIFIED DRUG;
EID: 34250762162     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-980358     Document Type: Article
Times cited : (8)
References (30)
  • 1
    • 0038106171 scopus 로고    scopus 로고
    • (a) Bloch, R. Chem. Rev. 1998, 98, 1407.
    • (1998) Chem. Rev , vol.98 , pp. 1407
    • Bloch, R.1
  • 23
    • 85064399949 scopus 로고    scopus 로고
    • Uno et al. observed very low yields (4% and 8%) of two different amine side products during their study on the addition of organolithium reagents to the O-tert-butyldimethylsilyl (TBDMS) derivative of an oxime in the presence of a Lewis acid: Uno, H.; Terakawa, T.; Suzuki, H. Synlett 1991, 559.
    • (a) Uno et al. observed very low yields (4% and 8%) of two different amine side products during their study on the addition of organolithium reagents to the O-tert-butyldimethylsilyl (TBDMS) derivative of an oxime in the presence of a Lewis acid: Uno, H.; Terakawa, T.; Suzuki, H. Synlett 1991, 559.
  • 24
    • 34250771327 scopus 로고    scopus 로고
    • The Yamamoto group3d has reported the N-O bond cleavage of oxime sulphonates by Grignard reagents to synthesize α
    • 3d has reported the N-O bond cleavage of oxime sulphonates by Grignard reagents to synthesize α,α- disubstituted amines.
    • alpha;- disubstituted amines
  • 26
    • 34250737064 scopus 로고    scopus 로고
    • The addition product 6a was the only product isolated (63%) when the first reaction was continued for one hour without the second addition.
    • The addition product 6a was the only product isolated (63%) when the first reaction was continued for one hour without the second addition.
  • 27
    • 34250706526 scopus 로고    scopus 로고
    • Typical procedure for the one-pot synthesis of amine 4m (Table 1, entry 14, The oxime ether 3d (100 mg, 0.67 mmol) was dissolved in dry toluene (5 mL) under N2 and cooled to -78°C. BF 3·Et2O (0.1 mL, 0.80 mmol) was added and the mixture was stirred for 15 min. PhLi (1.92 mol/L in n-butyl ether, 0.42 mL, 0.80 mmol) was added dropwise over 15 min. After 1 h, the reaction mixture was allowed to warm up to -20°C. Then n-BuLi (1.6 mol/L in n-hexane, 1.7 mL, 2.7 mmol) was added at -20°C and the mixture was stirred at r.t. for 0.5 h. The reaction mixture was quenched at 0°C with aq sat. NH4Cl solution (0.5 mL) and extracted with CHCl3 (3 x 10 mL, The extracts were combined, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by preparative TLC (n-hexane-EtOAc, 8: 1) to give the amine 4m (92 mg, 54, as a pale yellow oil. IR n
    • 23N: 253.1830; found: 253.1828.
  • 29
    • 34250747655 scopus 로고    scopus 로고
    • Typical procedure for the domino-type reaction in the synthesis of(diallyl)methylamine 8b (Table 3, entry 5, Allylmagnesium bromide (1 mol/L in Et2O, 1.8 mL, 1.8 mmol) was added to a r.t. solution of oxime ether 3f (110 mg, 0.46 mmol) in dry CH2Cl2 (2.3 mL, After being stirred at the same temperature for 45 min, the mixture was quenched with aq sat. NH4Cl solution (1 mL) at 0°C, extracted with CHCl3 (4 x 10 mL) and washed with brine. The organic phase was dried over MgSO4 and concentrated under reduced pressure. The oily mass was filtered through a short column of silica gel to give compound 8b (133.3 mg) in quantitative yield, as a colorless oil. IR (neat, 3376 cm-1; 1H NMR (300 MHz, CDCl3, δ, 7.46 (br d, J, 8.0 Hz, 2 H, 7.34 (br t, J, 8.0 Hz, 2 H, 7.24 (br t, J, 7.5 Hz, 1 H, 6.59 (br d, J, 8.5 Hz, 2 H, 6.28 br d
    • 23NO: 293.1779; found: 293.1782.
  • 30
    • 84944076963 scopus 로고    scopus 로고
    • Katritzky, A. R, Rees, C. W, Scriven, E. F, Newcome, G. R, Eds, Elsevier: Oxford, Chap. 9.01
    • Le Count, D. J. In Comprehensive Heterocyclic Chemistry, Vol. 9; Katritzky, A. R.; Rees, C. W.; Scriven, E. F.; Newcome, G. R., Eds.; Elsevier: Oxford, 1996, Chap. 9.01, 1-43.
    • (1996) Comprehensive Heterocyclic Chemistry , vol.9 , pp. 1-43
    • Le Count, D.J.1

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.