Functionalization of 2,3,4,5-Tetrahydro-1,5-benzodiazepin-2(1H)-ones by Electrophilic Aromatic Substitution

被引:0
|
作者
Regina Janciene
Ausra Vektariene
Zita Stumbreviciute
Lidija Kosychova
Kazimieras Konstantinavicius
Benedikta D. Puodziunaite
机构
[1] Institute of Biochemistry,
[2] LT-2600 Vilnius,undefined
[3] Lithuania,undefined
来源
Monatshefte für Chemie / Chemical Monthly | 2003年 / 134卷
关键词
Keywords. 2,3,4,5-Tetrahydro-1,5-benzodiazepin-2(1H)-ones; Electrophilic substitution; Hydrolysis; Semiempirical calculations.;
D O I
暂无
中图分类号
学科分类号
摘要
Highly substituted, novel, 8- and 9-nitro-2,3,4,5-tetrahydro-1,5-benzodiazepin-2(1H)-ones were obtained by direct nitration of the 7-bromo-5-trifluoroacetyl (or formyl)-substituted tetrahydrobenzodiazepinones. Alkaline and acidic hydrolysis of the novel mononitro derivatives was examined. Semiempirical AM1 calculations of aromatic substituents orientation in the nitration products are presented.
引用
收藏
页码:1629 / 1639
页数:10
相关论文
共 50 条
  • [1] Functionalization of 2,3,4,5-tetrahydro-1,5-benzodiazepin-2(1H)-ones by electrophilic aromatic substitution
    Janciene, R
    Vektariene, A
    Stumbreviciute, Z
    Kosychova, L
    Konstantinavicius, K
    Puodziunaite, BD
    MONATSHEFTE FUR CHEMIE, 2003, 134 (12): : 1629 - 1639
  • [2] Quantum chemical estimation of reactivity of 2,3,4,5-tetrahydro-1,5-benzodiazepin-2(1H)-ones in electrophilic aromatic substitution
    Vektariene, A
    Vektaris, G
    HETEROATOM CHEMISTRY, 2004, 15 (03) : 263 - 270
  • [3] 1,5-Benzodiazepin-2(3H)-ones: In Vitro Evaluation as Antiparkinsonian Agents
    Ortiz de Zarate, Ana
    Perez-Torralba, Marta
    Bonet Isidro, Inigo
    Lopez, Concepcion
    Claramunt, Rosa M.
    Martinez-Casanova, Diana
    Sanchez-Vera, Isabel
    Jimenez-Gonzalez, Jesus
    Lavandera, Jose Luis
    ANTIOXIDANTS, 2021, 10 (10)
  • [4] NOTE ON UNUSUAL BEHAVIOR OF 2,3,4,5-TETRAHYDRO-1,5-BENZOTHIAZEPIN-4-ONES DURING ARYLATION
    RIED, W
    SELL, G
    LIEBIGS ANNALEN DER CHEMIE, 1980, (11): : 1913 - 1916
  • [5] Investigations of alternative routes for 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepines
    Singer, RA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U131 - U132
  • [6] SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 2,3,4,5-TETRAHYDRO-1,5-METHANO-1H-3-BENZAZEPINES
    MAZZOCCHI, PH
    STAHLY, BC
    JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (04) : 455 - 457
  • [7] SYNTHESIS OF 2,3,4,5-TETRAHYDRO-1,2,4-TRIAZIN-3-ONES
    LOZANOVA, K
    SIMOV, D
    KALCHEVA, V
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1987, (09): : 1277 - 1279
  • [8] 4-Phenyl-1H-1,5-benzodiazepin-2(3H)-one
    Akkurt, Mehmet
    Kennedy, Alan R.
    Younes, Sabry H. H.
    Mohamed, Shaaban K.
    Abdelhamid, Antar A.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O3356 - +
  • [9] 4-Acetonylidene-1-ethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one
    Ould, MSMS
    Djerrari, B
    El Abbassi, M
    Fifani, J
    Essassi, EM
    El-Bali, B
    Bolte, M
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2000, 56 : E165 - E166
  • [10] 4-Acetonylidene-1-ethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one
    Ould, Mohammed Sydia Mohamed Said
    Djerrari, Bahia
    Abbassi, M'Barek El
    Fifani, Jilali
    Essassi, El-Mokhtar
    El-Bali, Brahim
    Bolte, Michael
    Acta Crystallographica Section C: Crystal Structure Communications, 2000, 56 (04)