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Volumn 7, Issue 2, 2009, Pages 325-334

Formylnitroenamines: Useful building blocks for nitrated pyridones and aminopyridines with functional groups

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CARBOXYLIC ACIDS; ESTERS; FUNCTIONAL GROUPS;

EID: 58049175874     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b815306j     Document Type: Article
Times cited : (17)

References (56)
  • 21
    • 58049147676 scopus 로고
    • Nitropyridones emplyed as dienophiles in Diels-Alder reaction:
    • P. F. H. Freeman, U.S. Pat., 197042858, 1970
    • (1970)
    • Freeman, P.F.H.1
  • 37
    • 0000121815 scopus 로고
    • The rearrangement of O-alkylpyridine: -258
    • S. Rozen D. Hebei Heterocycles 1989 28 249 258
    • (1989) Heterocycles , vol.28 , pp. 249
    • Rozen, S.1    Hebei, D.2
  • 47
    • 4644281075 scopus 로고
    • The fact that secondary amines such as diethylamine, morphorine, piperidine induced the formation of the pyridones suggests that the present reaction proceeds via an iminium salt intermediate formed by condensation between the formyl group of 1 and an amine. The formation of the reactive iminium ion is considered to enable the condensation with malonic acid derivatives 2 and 5 -1080
    • P. Barczynski H. C. van der Plas J. Org. Chem. 1982 47 1077 1080
    • (1982) J. Org. Chem. , vol.47 , pp. 1077
    • Barczynski, P.1    Van Der Plas, H.C.2
  • 48
    • 43849096211 scopus 로고    scopus 로고
    • 2= 0.1097 (all data) There are some reports that describe condensations of acetonitrile derivatives with carbonyl compounds without any base. Most of them were conducted at high temperatures, but the mechanism was not discussed: -2417
    • Y. Nakaike N. Taba S. Itoh Y. Tobe N. Nishiwaki M. Ariga Bull. Chem. Soc. Jpn. 2007 80 2413 2417
    • (2007) Bull. Chem. Soc. Jpn. , vol.80 , pp. 2413
    • Nakaike, Y.1    Taba, N.2    Itoh, S.3    Tobe, Y.4    Nishiwaki, N.5    Ariga, M.6
  • 54
  • 56
    • 0008540915 scopus 로고
    • In contrast to 8a and 8g, with less acidic acetonitrile derivatives 8b, 8c, 8d, 8e, and 8f, bases such as piperidine or potassium tert-butoxide were used to generate the corresponding anionic nucleophiles When triethylamine was employed as the tertiary amine in the reaction of 1a and 8e for 1 d at room temperature, aminopyridine 9j was formed in only 10% yield with 27% recovery of 1a, which indicates that piperidine serves not only as the base forming anionic nucleophiles but also as the activator of the formyl group of nitroenamine 1 by converting to iminium ion idrefs="cit25" 25
    • M. Wahren Z. Chem. 1966 6 181
    • (1966) Z. Chem. , vol.6 , pp. 181
    • Wahren, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.