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Volumn , Issue 15, 2003, Pages 2301-2304

A New Multicomponent Domino Reaction of 1,3-Dicarbonyl Compounds: One-Pot Access to Amino Azabicyclo[3.3.1]nonanones and 1,6-Hydronaphthyridines

Author keywords

1,3 dicarbonyls; 1,6 hydronaphthyridines; 1,6 trans diazadecalins; Azabicyclo 3.3.1 nonanes; Michael addition; Multicomponent domino reaction

Indexed keywords

1,3 DICARBONYL DERIVATIVE; 1,6 DIAZADECALIN DERIVATIVE; 1,6 HYDRONAPHTHYRIDINE DERIVATIVE; ACROLEIN; AMINE; AMINOAZABICYCLO[3.3.1]NONANONE DERIVATIVE; BETA KETO ESTER; BICYCLO COMPOUND; BICYCLO[3.3.1]NONANE DERIVATIVE; CARBONYL DERIVATIVE; DECALIN DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; NAPHTHYRIDINE DERIVATIVE; PIPERIDONE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

EID: 0348010521     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42121     Document Type: Article
Times cited : (25)

References (32)
  • 1
    • 33845375114 scopus 로고
    • see also refs. 2-10
    • For reviews on MCRs, see: Posner, G. H. Chem. Rev. 1986, 86, 831; see also refs. 2-10.
    • (1986) Chem. Rev. , vol.86 , pp. 831
    • Posner, G.H.1
  • 15
    • 0001157453 scopus 로고
    • (b) See also a special issue on heterogeneous catalysis: Hattori, H. Chem. Rev. 1995, 95, 475.
    • (1995) Chem. Rev. , vol.95 , pp. 475
    • Hattori, H.1
  • 17
    • 0007674230 scopus 로고
    • see also ref. 31
    • A similar effect on the substitution pattern at the nitrogen has been observed previously during the related condensation of acyclic β-ketoesters with 1-aza-1,3-butadienes: Geirsson, J. K. F.; Johannesdottir, J. F.; Jonsdotti, S. Synlett 1993, 133; see also ref. 31.
    • (1993) Synlett , pp. 133
    • Geirsson, J.K.F.1    Johannesdottir, J.F.2    Jonsdotti, S.3
  • 30
    • 0347182020 scopus 로고    scopus 로고
    • note
    • This 2D NMR study is part of: C. Simon; PhD Thesis; University Aix-Marseille III: France, 2001; and details will be published soon in a full paper.
  • 31
    • 0036795290 scopus 로고    scopus 로고
    • The Michael adduct can be obtained by reaction of 1 with acroleine in the presence of Dowex resins. When this 1,5-dicarbonyl intermediate reacts with primary amines, related naphthyridine derivatives 4 and azabicyclo[3.3.1] nonanones 5 are formed. For more experimental details, see: Simon, C.; Peyronel, J.-F.; Clerc, F.; Rodriguez, J. Eur. J. Org. Chem. 2002, 3359.
    • (2002) Eur. J. Org. Chem. , pp. 3359
    • Simon, C.1    Peyronel, J.-F.2    Clerc, F.3    Rodriguez, J.4
  • 32
    • 0029856245 scopus 로고    scopus 로고
    • Under these reaction conditions, another mechanistic pathway involving an imine resulting from acrolein and primary amine may be postulated. Nevertheless, although it is known that acyclic 1,3-dicarbonyls react with 3-substituted 1-aza-1,3-butadienes under acidic conditions, it has also been reported that simple enimines derived from acrolein or α,β- unsaturated ketones were not isolable. Therefore, these imines are likely not to be reactive intermediates in our MCR. For more details on such reported results, see: Geirsson, J. K. F.; Johannesdottir, J. F. J. Org. Chem. 1996, 61, 7320.
    • (1996) J. Org. Chem. , vol.61 , pp. 7320
    • Geirsson, J.K.F.1    Johannesdottir, J.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.