CONFORMATIONAL-ANALYSIS OF 4,5-DIHYDRO-1-PHENYL-1H-2,4-BENZODIAZEPINES

被引:5
|
作者
SANNER, MA
JOSEF, K
JOHNSON, RE
DAMBRA, T
KOWALCZYK, P
KULLNIG, RK
MICHAELS, F
机构
[1] STERLING WINTHROP INC,DEPT BIOPHYS & COMPUTAT CHEM,RENSSELAER,NY 12144
[2] EASTMAN KODAK CO,DIV ANALYT TECHNOL,ROCHESTER,NY 14626
来源
JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 23期
关键词
D O I
10.1021/jo00075a042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Detailed conformational analysis of 1-phenyl-1H-4,5-dihydro-2,4-benzodiazepines using X-ray structures, nuclear Overhauser experiments, variable-temperature H-1 NMR, and MacroModel (MULTIC) reveals a rapid equilibrium between axial and equatorial comformations for the free base of 2. The DCl salt of 2 and 1-methyl-1-phenyl analog 3, however, prefer the axial conformation.
引用
收藏
页码:6417 / 6420
页数:4
相关论文
共 50 条
  • [21] 1-(4-Methylphenylsulfonyl)-5-phenyl-4,5-dihydro-1H-pyrazole
    Li, Jie
    Zhao, Wei
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1898 - U1752
  • [22] 1,3-DIOXOLO[4,5-H][1, 4]BENZODIAZEPINES
    GAKHAR, HK
    SANGAR, N
    AGGARWAL, S
    ARORA, GS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1995, 34 (12): : 1089 - 1091
  • [23] A NEW METHOD FOR PREPARING 5-ARYL-2,3-DIHYDRO-1H-1,4-BENZODIAZEPINES
    SULKOWSKI, TS
    CHILDRESS, SJ
    JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (08): : 2150 - &
  • [24] CONFORMATIONAL-ANALYSIS OF AROMATIC DERIVATIVES OF 2,3-DIHYDRO-1H-1,5-BENZODIAZEPINE
    ORLOV, VD
    KOLOS, NN
    ABRAMOV, AF
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1984, (12): : 1662 - 1666
  • [25] STUDIES ON DIAZEPINES .21. PHOTOCHEMICAL-SYNTHESIS OF 1H-2,4-BENZODIAZEPINES FROM 4-AZIDOISOQUINOLINES
    SAWANISHI, H
    SASHIDA, H
    TSUCHIYA, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1985, 33 (10) : 4564 - 4571
  • [26] CONFORMATIONAL-ANALYSIS AND H-1 SPECTRA OF 1-PYRAZOLINES
    TOUILLAUX, R
    TINANT, B
    VANMEERSSCHE, M
    DEREPPE, JM
    LEROY, G
    WEILER, J
    JOURNAL DE CHIMIE PHYSIQUE ET DE PHYSICO-CHIMIE BIOLOGIQUE, 1980, 77 (04) : 319 - 324
  • [27] CENTRAL NERVOUS-SYSTEM ACTIVITY OF A NOVEL CLASS OF ANNELATED 1,4-BENZODIAZEPINES, AMINOMETHYLENE-2,4-DIHYDRO-1H-IMIDAZO[1,2-A][1,4]BENZODIAZEPIN-1-ONES
    AGER, IR
    DANSWAN, GW
    HARRISON, DR
    KAY, DP
    KENNEWELL, PD
    TAYLOR, JB
    JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (08) : 1035 - 1041
  • [28] 4,5-dihydro-3-methyl-5-(4-methyl-phenyl)-1H-pyrazole-1-carboxamide
    Kettmann, V
    Svetlík, J
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2003, 59 : O419 - O421
  • [29] 1-{5-[4-(Hexyloxy)phenyl]-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl}ethanone
    Abbas, Asghar
    Hussain, Safdar
    Hafeez, Noureen
    Lo, Kong Mun
    Hasan, Aurangzeb
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2010, 66 : O2505 - U1872
  • [30] A simple and one-pot synthesis of 2,3,4,5-tetrasubstituted 4,5-dihydro-3H-1,4-benzodiazepines
    Wang, Ying
    Chen, Min
    Ding, Ming-Wu
    TETRAHEDRON, 2013, 69 (43) : 9056 - 9062