메뉴 건너뛰기




Volumn 70, Issue 23, 2005, Pages 9463-9469

Efficient regioselective synthesis of 6-amino-5-benzoyl-1-substituted 2 (1H)-pyridinones

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CHEMICAL BONDS; DEFORMATION; ESTERS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 27744509094     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0515428     Document Type: Article
Times cited : (53)

References (53)
  • 1
  • 27
    • 27744554530 scopus 로고    scopus 로고
    • The synthesis of 6-amino-5-benzoyl-4-methyl-1-phenylpyridin-2(1H)-one was described in the following: Wardakhan, W. W.; Agami, S. M. Egypt J. Chem. 2001, 44, 315-333.
    • (2001) Egypt J. Chem. , vol.44 , pp. 315-333
    • Wardakhan, W.W.1    Agami, S.M.2
  • 30
    • 27744561316 scopus 로고    scopus 로고
    • β-Amino-β-imino acid esters. British Patent DT 1,409,987, Jan 31, 1974
    • (a) Meier, E.; Glockner, H.; Kuffner, K.; Boie, I. β-Amino-β- imino acid esters. British Patent DT 1,409,987, Jan 31, 1974.
    • Meier, E.1    Glockner, H.2    Kuffner, K.3    Boie, I.4
  • 32
    • 0000969814 scopus 로고
    • An alternative synthesis was published in the following: Woodman, D. J.; Murphy, Z. L. J. Org. Chem. 1969, 34, 3451-3456.
    • (1969) J. Org. Chem. , vol.34 , pp. 3451-3456
    • Woodman, D.J.1    Murphy, Z.L.2
  • 33
    • 0034629167 scopus 로고    scopus 로고
    • For further methods for N,N′-disubstituted ketene aminals from activated methylene compounds and isothiocyanates, see: (a) Barun, O.; Ila, H.; Junjappa, H.; Singh, O. M. J. Org. Chem. 2000, 65, 1583-1587.
    • (2000) J. Org. Chem. , vol.65 , pp. 1583-1587
    • Barun, O.1    Ila, H.2    Junjappa, H.3    Singh, O.M.4
  • 35
    • 0001656259 scopus 로고    scopus 로고
    • The chloroform must be ethanol free. When ethanol-stabilized chloroform was used, the product contained a substantial amount of the ethyl imidoate. This compound was transformed into the desired amidine in low yield, see also ref 11 and Shilcrat, S. C.; Mokhallalati, M. K.; Fortunak, J. M. D.; Pridgen, L. N. J. Org. Chem. 1997, 62, 8449-8454.
    • (1997) J. Org. Chem. , vol.62 , pp. 8449-8454
    • Shilcrat, S.C.1    Mokhallalati, M.K.2    Fortunak, J.M.D.3    Pridgen, L.N.4
  • 37
    • 0141775420 scopus 로고    scopus 로고
    • For a similar reaction of enaminones with propiolic ester leading to N-aryl pyridinones, see: Savarin, C. G.; Murry, J. A.; Dormer, P. G. Org. Lett. 2002, 4, 2071-2074.
    • (2002) Org. Lett. , vol.4 , pp. 2071-2074
    • Savarin, C.G.1    Murry, J.A.2    Dormer, P.G.3
  • 38
    • 27744521249 scopus 로고    scopus 로고
    • in press
    • We reported on the application of in-situ-generated propiolic acid chloride in a similar reaction, see: Schirok, H.; Alonso-Alija, C.; Michels, M. Synthesis 2005, in press.
    • (2005) Synthesis
    • Schirok, H.1    Alonso-Alija, C.2    Michels, M.3
  • 41
    • 27744590887 scopus 로고    scopus 로고
    • note
    • Column: KBD 6175, 250 mm × 20 mm. Eluent: isohexane/ethyl acetate 60:40. Temperature: 23 °C. Flow: 15 mL/min. UV detection: 254 nm.
  • 42
    • 27744523582 scopus 로고    scopus 로고
    • note
    • 1/2 (25 °C) = 4054 years.
  • 43
    • 0002633516 scopus 로고
    • Ernst, L. ChiuZ 1983, 17, 21-30.
    • (1983) ChiuZ , vol.17 , pp. 21-30
    • Ernst, L.1
  • 49


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.