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Volumn , Issue 9, 2005, Pages 1437-1441

Aza-annulation of polarized N,S- and N,N-ketene acetals with itaconic anhydride: Synthesis of novel functionalized 1,2,3,4-tetrahydro-2-pyridones and related azabicycles

Author keywords

Alkaloids; Annulation; Esters; Heterocycles; Lactams; Michael addition; Nitriles

Indexed keywords

1,2,3,4 TETRAHYDRO 2 PYRIDONE DERIVATIVE; ACETAL; ACID ANHYDRIDE; BICYCLO COMPOUND; HETEROCYCLIC COMPOUND; ITACONIC ACID; KETENE DERIVATIVE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 20544444006     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-868491     Document Type: Article
Times cited : (58)

References (53)
  • 5
    • 0000166457 scopus 로고    scopus 로고
    • Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: New York, Chap. 5
    • (e) Balasubramaniam, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: New York, 1996, Chap. 5, 245.
    • (1996) Comprehensive Heterocyclic Chemistry II , pp. 245
    • Balasubramaniam, M.1    Keay, J.G.2
  • 26
    • 11144239452 scopus 로고    scopus 로고
    • Gribble, G. W.; Gilchrist, T. L., Eds.; Pergamon: New York, Chap. 1
    • (c) Ila, H.; Junjappa, H.; Mohanta, P. K. Progress in Heterocyclic Chemistry, Vol. 13; Gribble, G. W.; Gilchrist, T. L., Eds.; Pergamon: New York, 2001, Chap. 1, 1.
    • (2001) Progress in Heterocyclic Chemistry , vol.13 , pp. 1
    • Ila, H.1    Junjappa, H.2    Mohanta, P.K.3
  • 47
    • 20544454519 scopus 로고    scopus 로고
    • note
    • General procedure for the aza-annulation of acyclic and cyclic α-oxo- and α-nitro N,S- and N,N-ketene acetals with itaconic anhydride: A solution of the appropriate N,S- or N,N-ketene acetal (1 mmol) and itaconic anhydride (0.12 g, 1.1 mmol) in anhyd acetonitrile (30 mL) was refluxed under a nitrogen atmosphere for 8-10 h (monitored by TLC). The reaction mixture was concentrated under reduced pressure and the residue was subjected to column chromatography over silica gel using hexane-EtOAc (4:1) (4a-f, 6a,b, 8a-f, 12, 14) as eluent to give pure compounds.
  • 51
    • 20544447708 scopus 로고    scopus 로고
    • Note
    • X-ray crystallographic data of structure 12 has been deposited at the Cambridge Crystallographic Data Centre and has been allocated the deposition number CCDC 268032.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.