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Volumn 76, Issue 2, 2008, Pages 1017-1022

An easy access to the exocyclic lactams analogous of the central nervous system active tricyclic nitroxapine, mianserine and chlothiapine agents using N-acyliminium chemistry

Author keywords

Cationic Cyclization; CNS Activity; Dibenzo(thia, oxa or a)zepine; N Acyliminium Ion

Indexed keywords


EID: 61349124307     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(N)97     Document Type: Article
Times cited : (22)

References (23)
  • 9
    • 0027947142 scopus 로고
    • Drug treatment of schizophrenia has advanced significantly with the discovery of Clozapine but unfortunately causes agranulocytosis. For this end, see
    • Drug treatment of schizophrenia has advanced significantly with the discovery of Clozapine but unfortunately causes agranulocytosis. For this end, see. Lowe J.A. Curr. Med. Chem. 1 (1994) 50
    • (1994) Curr. Med. Chem. , vol.1 , pp. 50
    • Lowe, J.A.1
  • 19
    • 33745751548 scopus 로고    scopus 로고
    • For recent paper in this area, see:
    • For recent paper in this area, see:. Zhang W., Huang L., and Wang J. Synthesis (2006) 2053
    • (2006) Synthesis , pp. 2053
    • Zhang, W.1    Huang, L.2    Wang, J.3
  • 20
    • 61349188742 scopus 로고    scopus 로고
    • 2, AcOEt/cyclohexane (4:1)] and recrystallized from the indicated solvents to give the expected tricyclic product.
    • 2, AcOEt/cyclohexane (4:1)] and recrystallized from the indicated solvents to give the expected tricyclic product.
  • 21
    • 61349193589 scopus 로고    scopus 로고
    • Selected data for 1,2,3,13b-tetrahydropyrrolo[1,2-d]dibenzo[b,f][1,4]oxazepin-3-one (4a, This compound was isolated as a white solid in 84% yield after recrystallization from Et2O and melted at 127 °C; IR (KBr) v 1711 cm-1; 1H-NMR (CDCl3) δ 2.22-2.44 (m, 1H, Hpyrrolidine, 2.47-2.71 (m, 3H, Hpyrrolidine, 5.28-5.39 (m, 1H, CH, 7.07-7.28 (m, 7H, Haromatic, 7.72 (d, 1H, J=8.3 Hz, Haromatic, 13C-NMR (CDCl3) δ 27.1 (CH2, 31.3 (CH2, 60.4 (CH, 121.8 (CH, 125.0 (CH, 125.1 (CH, 125.2 (CH, 126.6 (CH, 127.0 (CH, 127.6 (CH, 129.5 (CH, 130.4 (Cq, 130.9 (Cq, 151.6 (Cq, 155.7 (Cq, 174.1 (CO, MS (El, 70 ev) m/z: 251 (M, Anal. Calcd for C16H13NO2 251.28, C, 76.48; H, 5.21; N, 5.57. Found: C, 76.31; H, 5.09; N, 5.48
    • 2 (251.28): C, 76.48; H, 5.21; N, 5.57. Found: C, 76.31; H, 5.09; N, 5.48.
  • 22
    • 61349161507 scopus 로고    scopus 로고
    • Selected data for 1,2-dihydropyrrolo[1,2-d]dibenzo[b,f][1,4]oxazepin-3-one (5a, This product was isolated as a white solid in 64% yield after recrystallization from Et2O/cyclohexane and melted at 115 °C; IR (KBr) v 1712 cm-1; 1H-NMR (CDCl3) δ 3.40 (s, 2H, CH2-C, 5.60 (s, 1H, CH{double bond, long}C, 7.13-7.42 (m, 6H, Haromatic, 7.52 (d, l H, J=7.6 Hz, Haromatic, 7.87 (d, I H, J=7.6 Hz, Haromatic, 13C-NMR (CDCl3) δ 37.5 (CH2, 102.3 (CH{double bond, long, 121.0 (CH, 121.8 (CH, 125.5 (CH, 125.6 (CH, 125.7 (CH, 127.0 (Cq, 127.3 (CH, 128.6 (CH, 129.0 (Cq, 131.2 (CH, 142.5 (Cq, 151.5 (Cq, 156.6 (Cq, 176.1 (CO, MS (EI, 70 ev) m/z: 249 (M, Anal. Calcd for C16H11NO2 249.27, C 77.10; H 4.45; N 5.62. Found: C 76.92; H 4.30; N 5.48
    • 2 (249.27): C 77.10; H 4.45; N 5.62. Found: C 76.92; H 4.30; N 5.48.
  • 23
    • 61349194837 scopus 로고    scopus 로고
    • Selected data for 1-methyl-3,13b-dihydropyrrolo[1,2-d]dibenzo[b,f][1,4]oxazepin-3-one (6Ua, This product was isolated as a white solid in 65% yield after recrystallization from Et2O/hexane and melted at 159 °C; IR (KBr) v 1687 cm-1; 1H-NMR (CDCl3) δ 2.07 (d, 3H, J=1.3 Hz, CH3(CH, 6.11 (q, 1H, J=1.3 Hz, CH(CH3, 6.96-7.17 (q, 4H, Haromatic+CH{double bond, long}C, 7.20-7.35 (m, 4H, Haromatic, 8.85 (d, 1H, J=7.6 Hz, Haromatic, 13C-NMR (CDCl3) δ 11.6 (CH3, 60.7 (CH, 120.7 (CH, 121.3 (CH, 122.0 (CH, 125.0 (CH, 125.2 (CH, 125.3 (CH, 126.8 (CH, 129.5 (Cq, 130.6 (CH, 131.2 (Cq, 137.5 (CH, 137.7 (Cq, 146.1 (Cq, 156.6 (Cq, 169.9 (CO, MS (El, 70 ev) m/z: 263 (M, Anal. Calcd for C17H13NO2 263.29, C 77.55; H 4.98; N 5.32. Found: C 77.33; H 4.76; N 5.16
    • 2 (263.29): C 77.55; H 4.98; N 5.32. Found: C 77.33; H 4.76; N 5.16.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.