Novel application of Leuckart-Wallach reaction for synthesis of tetrahydro-1,4-benzodiazepin-5-ones library

被引:55
|
作者
Lee, Sung-Chan [1 ]
Park, Seung Bum [1 ]
机构
[1] Seoul Natl Univ, Dept Chem, Seoul, South Korea
关键词
PHARMACOLOGICAL ACTIVITY; INHIBITORS; DERIVATIVES; BENZODIAZEPINE; ANTHRAMYCIN; DESIGN;
D O I
10.1039/b709768a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and efficient strategy has been developed to synthesize privileged tetrahydro-1,4-benzodiazepines with excellent yields and purities; this synthetic pathway was established by the revitalization of the Leuckart-Wallach(LW) reaction via solidphase synthesis.
引用
收藏
页码:3714 / 3716
页数:3
相关论文
共 38 条
  • [21] A novel route to pyrrolo[2,1-c][1,4]benzodiazepin-5-ones.: Formal total synthesis of (±)-DC-81
    Wang, TS
    Lui, AS
    Cloudsdale, IS
    ORGANIC LETTERS, 1999, 1 (11) : 1835 - 1837
  • [22] Synthesis and anti-HIV activity of 1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one (TBO) derivatives.: Truncated 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-ones (TIBO) analogues
    Breslin, HJ
    Kukla, MJ
    Kromis, T
    Cullis, H
    De Knaep, F
    Pauwels, R
    Andries, K
    De Clercq, E
    Janssen, MAC
    Janssen, PAJ
    BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (11) : 2427 - 2436
  • [23] Synthesis of Chiral 3-Substituted 1,3,4,5-Tetrahydro-1,4-benzodiazepin-2-ones via a Domino Copper-Catalyzed SN2/Coupling Reaction
    Lu, Dongming
    Ma, Chang
    Yuan, Shuai
    Zhou, Lihong
    Zeng, Qingle
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (16-17) : 3491 - 3494
  • [24] REGIOSELECTIVITY OF THE REACTION OF ORGANOZINC COMPOUNDS WITH ALPHA-IMINOESTERS DERIVED FROM 2-AMINO OR 3-AMINO ALCOHOLS .2. SYNTHESIS OF 3-SUBSTITUTED HEXAHYDRO-1,4-OXAZEPIN-2-ONES AND TETRAHYDRO-1,4-OXAZIN-2-ONES
    COURTOIS, G
    MIGINIAC, L
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 452 (1-2) : 5 - 12
  • [25] A novel, microwave-assisted method for the synthesis of alicyclic-condensed 5H-1,4,6,7-tetrahydro-1,4-diazepin-5-ones
    Balazs, Arpad
    Van der Eycken, Erik
    Fulop, Ferenc
    TETRAHEDRON LETTERS, 2008, 49 (28) : 4333 - 4335
  • [26] A Schmidt rearrangement-mediated synthesis of novel tetrahydro-benzo[1,4]diazepin-5-ones as potential anticancer and antiprotozoal agents
    Insuasty, Daniel
    Robledo, Sara M.
    Velez, Ivan D.
    Cuervo, Paola
    Insuasty, Braulio
    Quiroga, Jairo
    Nogueras, Manuel
    Cobo, Justo
    Abonia, Rodrigo
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 141 : 567 - 583
  • [27] Synthesis of chiral 3,4,5,6-tetrahydro-1,4-thiazin-2-ones (thiamorpholin-2-ones)-novel heterocycles possessing enhanced carbonyl electrophilicity over their oxygen counterparts
    Drew, Michael G. B.
    Harwood, Laurence M.
    Yan, Ran
    SYNLETT, 2006, (19) : 3259 - 3262
  • [28] NOVEL SYNTHESIS OF 5,11-DIHYDRO-6H-PYRIDO[2,3-B]-[1,4]BENZODIAZEPIN-6-ONES AND RELATED STUDIES .1.
    OKLOBDZIJA, M
    COMISSO, G
    DECORTE, E
    FAJDIGA, T
    GRATTON, G
    MOIMAS, F
    TOSO, R
    SUNJIC, V
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (05) : 1329 - 1334
  • [29] FACILE SYNTHESIS OF 1,4-BENZODIAZEPIN-5-ONE DERIVATIVES VIA INTRAMOLECULAR AZA-WITTIG REACTION - APPLICATION TO AN EFFICIENT SYNTHESIS OF O-BENZYL DC-81
    EGUCHI, S
    YAMASHITA, K
    MATSUSHITA, Y
    KAKEHI, A
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13): : 4006 - 4012
  • [30] APPLICATION OF THE PHOTO-FRIES REARRANGEMENT OF ARYL N-CHLOROACETYLANTHRANYLATES AS KEY STEP IN THE SYNTHESIS OF 5-(2-HYDROXYPHENYL)-1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES
    ALGARRA, F
    MIRANDA, MA
    HETEROCYCLES, 1993, 36 (10) : 2335 - 2344