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Volumn 41, Issue 14, 2000, Pages 2309-2312

Intramolecular cyclization of aromatic imines: An approach to tetrahydrochromano[4,3-b]quinolines

Author keywords

Acridines; Cycloadditions; Imines

Indexed keywords

AROMATIC AMINE; QUINOLINE DERIVATIVE;

EID: 0034175538     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00156-8     Document Type: Article
Times cited : (31)

References (34)
  • 3
    • 0000048258 scopus 로고
    • (c) Paquette, L. A., Ed.; Pergamon: Oxford
    • (c) Oppolzer, W. In Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon: Oxford, 1991; Vol. 5, p. 315;
    • (1991) In Comprehensive Organic Synthesis , vol.5 , pp. 315
    • Oppolzer, W.1
  • 23
    • 0030602266 scopus 로고    scopus 로고
    • For synthesis of tetrahydroquinolines and their biological activity see for example: and references cited therein
    • For synthesis of tetrahydroquinolines and their biological activity see for example: Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031 and references cited therein.
    • (1996) Tetrahedron , vol.52 , pp. 15031
    • Katritzky, A.R.1    Rachwal, S.2    Rachwal, B.3
  • 31
    • 0342795587 scopus 로고    scopus 로고
    • Note
    • 4: 339.1471. Found: 339.1472.
  • 32
    • 0000173004 scopus 로고
    • Several related derivatives of salicylic aldehyde, namely A, B, C and D were applied as substrates for the intramolecular [4+2] cycloaddition reaction with anilines under the conditions described above. However, the only product detected in the reaction mixture was the corresponding non-cyclized imine. Attempts to cyclize it under a variety of experimental conditions, including elevated temperatures and various catalysts were not successful. This result may be attributed to the insufficient electron density on the olefinic fragment of A-C, and to the unfavorable thermodynamics for the formation of the [6,7] fused system for D. Similar difficulties in the intramolecular cycloaddition reactions for the formation of [6,7] fused systems have been reported, see for example
    • Several related derivatives of salicylic aldehyde, namely A, B, C and D were applied as substrates for the intramolecular [4+2] cycloaddition reaction with anilines under the conditions described above. However, the only product detected in the reaction mixture was the corresponding non-cyclized imine. Attempts to cyclize it under a variety of experimental conditions, including elevated temperatures and various catalysts were not successful. This result may be attributed to the insufficient electron density on the olefinic fragment of A-C, and to the unfavorable thermodynamics for the formation of the [6,7] fused system for D. Similar difficulties in the intramolecular cycloaddition reactions for the formation of [6,7] fused systems have been reported, see for example: (a) Wu, H.-J.; Lin, S.-H.; Lin, C.-C. Heterocycles 1994, 38, 1507;
    • (1994) Heterocycles , vol.38 , pp. 1507
    • Wu, H.-J.1    Lin, S.-H.2    Lin, C.-C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.