메뉴 건너뛰기




Volumn , Issue 13, 2004, Pages 2331-2334

Synthesis of xantheno[1,9-cd]azepines: Electrophilic cyclization of carbamates and N-acyliminium ions

Author keywords

2 Benzazepines; Cyclization of carbamates; N acyliminium ions; Pyrrolo 1,2 a xantheno 1,9 cd azepines; Xantheno 1,9 cd azepines

Indexed keywords

ACYLIMINIUM ION; AZEPINE DERIVATIVE; BENZAZEPINE DERIVATIVE; CARBAMIC ACID DERIVATIVE; IMINE; PYRROLE DERIVATIVE; PYRROLO[1,2 A]XANTHENO[1,9 CD]AZEPINE; UNCLASSIFIED DRUG; XANTHENO[1,9 CD]AZEPINE;

EID: 8644234210     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-832825     Document Type: Article
Times cited : (7)

References (30)
  • 10
    • 8644282262 scopus 로고    scopus 로고
    • note
    • All new compounds were fully characterized spectroscopically and had satisfactory elemental analyses or HRMS data.
  • 13
    • 0010162574 scopus 로고
    • Although the Bischler-Napieralski cyclization of secondary formamides is very effective for the formation of six-membered rings, it is generally less useful for the synthesis of 2-benzazepines, low yields having frequently been reported: (a) Alonso, R.; Takahashi, K.; Schönenberger, B.; Brossi, A. Heterocycles 1987, 26, 1595.
    • (1987) Heterocycles , vol.26 , pp. 1595
    • Alonso, R.1    Takahashi, K.2    Schönenberger, B.3    Brossi, A.4
  • 17
    • 0037043540 scopus 로고    scopus 로고
    • Some recent examples of electrophilic cyclization of carbamates leading to isoquinolones: (a) Wang, Y. C.; Georghiou, P. E. Org. Lett. 2002, 4, 2675.
    • (2002) Org. Lett. , vol.4 , pp. 2675
    • Wang, Y.C.1    Georghiou, P.E.2
  • 23
    • 8644286980 scopus 로고
    • A 15% yield has been reported in the cyclization of a secondary carbamate: Potapov, V. M.; Dem'yanovich, V. M.; Solov'eva, L. D.; Vendrova, O. E. Khim. Geterotsikl. Soedin. 1981, 5, 675; Chem. Abstr. 1981, 95, 132135.
    • (1981) Chem. Abstr. , vol.95 , pp. 132135
  • 24
    • 8644287723 scopus 로고    scopus 로고
    • note
    • + - OMe]: 306.1494; found: 306.1502.
  • 25
    • 84985283644 scopus 로고
    • Tertiary amides, which cannot form nitrilium ions under the Bischler-Napieralski reaction conditions, are known not to afford seven-membered rings under these conditions: Schlüter, G.; Meise, W. Liebigs Ann. Chem. 1988, 833.
    • (1988) Liebigs Ann. Chem. , pp. 833
    • Schlüter, G.1    Meise, W.2
  • 26
    • 46549103031 scopus 로고
    • Cyclization by intramolecular amidoalkylation of aromatics with reactive N-acyliminium ions allows the synthesis of a variety of benzofused heterocyclic systems: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
    • (1985) Tetrahedron , vol.41 , pp. 4367
    • Speckamp, W.N.1    Hiemstra, H.2
  • 28
    • 8644285280 scopus 로고    scopus 로고
    • note
    • 3: C, 74.75; H, 5.96; N, 4.36. Found: C, 74.57; H, 5.77; N, 4.41.
  • 29
    • 0034743059 scopus 로고    scopus 로고
    • and references therein
    • (a) There are only a few known examples of N-acyliminium cyclizations leading to seven-membered benzofused heterocycles: Bahajaj, A. A.; Vernon, J. M.; Wilson, G. D. J. Chem. Soc., Perkin Trans. 1 2001, 1446; and references therein.
    • (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 1446
    • Bahajaj, A.A.1    Vernon, J.M.2    Wilson, G.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.