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Volumn , Issue 30, 2007, Pages 4995-4998

Synthesis of spirocyclic pyridoazepines as analogues of galanthamine by nucleophilic aromatic substitution of 3-substituted 2-chloropyridines

Author keywords

Acetylcholinesterase; Amines; Nitrogen heterocycles; Nucleophilic aromatic substitution; Spiro compounds

Indexed keywords


EID: 35548961862     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700614     Document Type: Article
Times cited : (12)

References (29)
  • 19
    • 35548959813 scopus 로고    scopus 로고
    • Spectroscopic data for compound 10a: 1H NMR (400 MHz, CDCl3, δ, 7.69 (s, 1 H, 3.54 (s, 2 H, 3.29 (dd, J, 8.4, 5.4 Hz, 2 H, 2.85 (s, 3 H, 2.55 (t, J, 7.5 Hz, 2 H, 2.51-2.45 (m, 1 H, 2.36 (s, 3 H, 2.24 (s, 3 H, 2.18-2.12 (m, 2 H, 1.72-1.58 (m, 1 H, 1.57-1.45 (m, 1 H) ppm. 13C NMR (100 MHz, CDCl3, δ, 176.9, 148.6, 147.0, 142.5, 132.8, 131.8, 57.9, 55.9, 48.0, 42.6, 40.0, 30.1, 29.6, 25.5, 19.3 ppm. HRMS: calcd. for C15H21Cl 2N3O 329.1062; found 329.1063. Spectroscopic data for compound 10b: 1H NMR (400 MHz, CDCl3, δ, 7.62 (s, 1 H, 3.46 (s, 2 H, 3.28-3.18 (m, 2 H, 2.92 (s, 3 H, 2.52-2.42 (m, 2 H, 2.35-2.28 (m, 1 H, 2.26 (s, 3 H, 2.18 (s, 3 H, 1.90-1.80 (m, 2 H, 1.76-1.66 (m, 1 H, 1.55-1.40 (m, 3 H) ppm. 13C NMR 100 MHz, CDCl3, δ, 172.9, 148.4, 146.9, 142.7, 132.8, 131.8, 57.7, 5
    • 3O 343.1218; found 343.1210.
  • 20
    • 35548976890 scopus 로고    scopus 로고
    • CEM-Discover, CEM Corporation P. O. Box 200 Matthews, NC 28106.
    • CEM-Discover, CEM Corporation P. O. Box 200 Matthews, NC 28106.
  • 21
    • 35548950082 scopus 로고    scopus 로고
    • 4 and concentrated under reduced pressure.
    • 4 and concentrated under reduced pressure.
  • 22
    • 35548937130 scopus 로고    scopus 로고
    • Spectroscopic data for compound 2a: 1H NMR (400 MHz, CDCl3, δ, 7.24 (s, 1 H, 4.20 (d, J, 14.6 Hz, 1 H, 3.62 (d, J, 14.6 Hz, 1 H, 3.46 (dd, J, 16.3, 9 Hz, 1 H, 3.30 (td, J, 9, 3.4 Hz, 1 H, 3.11-3.05 (m, 1 H, 3.02-2.95 (m, 1 H, 2.92 (s, 3 H, 2.73-2.65 (m, 1 H, 2.47 (s, 3 H, 2.48-2.40 (m, 1 H, 2.29 (s, 3 H, 2.09 (dt, J, 13, 8 Hz, 1 H, 1.85-1.80 (m, 1 H) ppm. 13C NMR 100 MHz CDCl3, δ, 176.6, 158.8, 148.5, 141.9, 130.1, 58.2, 55.1, 54.0, 46.8, 43.9, 32.3, 32.1, 30.1, 18.8 ppm. HRMS: calcd. for C 15H20ClN3O 293.1295; found 293.1297. Spectroscopic data for compound 2b: HRMS: calcd. for C16H 22ClN3O 307.1451; found 307.1448
    • 3O 307.1451; found 307.1448.
  • 23
    • 35548950711 scopus 로고    scopus 로고
    • This ring closure was carried out at 80°C for 10 min instead of 100°C for 15 min. At 100°C, compound 2b could not be detected
    • This ring closure was carried out at 80°C for 10 min instead of 100°C for 15 min. At 100°C, compound 2b could not be detected.
  • 24
    • 35548948673 scopus 로고    scopus 로고
    • 2 268.0978; found 268.0971.
    • 2 268.0978; found 268.0971.
  • 25
    • 35548957097 scopus 로고    scopus 로고
    • 4.
    • 4.
  • 26
    • 35548992136 scopus 로고    scopus 로고
    • 2 321.1244; found 321.1249.
    • 2 321.1244; found 321.1249.
  • 27
    • 35548964903 scopus 로고    scopus 로고
    • 3O 293.1295; found 293.1293.
    • 3O 293.1295; found 293.1293.
  • 28
    • 35548981597 scopus 로고    scopus 로고
    • 2 307.1088; found 307.1097.
    • 2 307.1088; found 307.1097.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.