Novel access to 1,4-benzodiazepin-2-ones via the Buchwald reaction and application to the synthesis of novel heterocyclics

被引：8
|
作者：
Salome, Christophe [1 ]
Schmitt, Martine [1 ]
Bourguignon, Jean-Jacques [1 ]
机构：
[1] Fac Pharm, Lab Innovat Therapeut, UMR 7200, F-67401 Illkirch Graffenstaden, France
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 09期
关键词：
Buchwald; Pd crosscoupling; 1,4-Benzodiazepin-2-one; Pyridine; Pyridazine; ARYL HALIDES;
D O I：
10.1016/j.tetlet.2011.12.045
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new two step strategy for the preparation of 1,4-benzodiazepin-2-ones has been developed starting from the 2-halogenobenzophenone under Buchwald conditions (Pd(OAc)(2), XantPhos, Cs2CO3, dioxane 100 degrees C). This strategy has been extended to two 2-halogeno-3-benzoyl-azines (pyridines, pyridazines). (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1033 / 1035
页数：3
相关论文
共 50 条
  • [21] RELATIONSHIP BETWEEN GEOMETRICAL CHARACTERISTICS AND ANTICONVULSIVE ACTIVITY OF 1,4-BENZODIAZEPIN-2-ONES
    ANDRONATI, SA
    PROKOPENKO, IA
    YAVORSKY, AS
    SIMONOV, YA
    DVORKIN, AA
    GIFEISMAN, TS
    CHEPELEV, VM
    PHARMAZIE, 1988, 43 (10): : 730 - 731
  • [22] CHIRAL 1,4-BENZODIAZEPIN-2-ONES - RELATIONSHIP BETWEEN STEREOCHEMISTRY AND PHARMACOLOGICAL ACTIVITY
    SALVADORI, P
    BERTUCCI, C
    DOMENICI, E
    GIANNACCINI, G
    JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1989, 7 (12) : 1735 - 1742
  • [23] Enantioselective synthesis of diversely substituted quaternary 1,4-benzodiazepin-2-ones and 1,4-benzodiazepine-2,5-diones
    Carlier, Paul R.
    Zhao, Hongwu
    MacQuarrie-Hunter, Stephanie L.
    DeGuzman, Joseph C.
    Hsu, Danny C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (47) : 15215 - 15220
  • [24] Novel application of Leuckart-Wallach reaction for synthesis of tetrahydro-1,4-benzodiazepin-5-ones library
    Lee, Sung-Chan
    Park, Seung Bum
    CHEMICAL COMMUNICATIONS, 2007, (36) : 3714 - 3716
  • [25] SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF 1-ALKOXYALKYL- AND 1-ARYLOXYALKYL-1,4-BENZODIAZEPIN-2-ONES
    LAMDAN, S
    GAOZZA, CH
    SICARDI, S
    IZQUIERD.JA
    JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (04) : 742 - &
  • [26] CONVENIENT SYNTHESIS OF 5-SUBSTITUTED 1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES
    OGATA, M
    MATSUMOTO, H
    CHEMISTRY & INDUSTRY, 1976, (24) : 1067 - 1068
  • [27] A novel synthesis of 1,3-benzodiazepin-2-ones using intramolecular Heck reaction
    Hayashi, M
    Sai, H
    Horikawa, H
    HETEROCYCLES, 1998, 48 (07) : 1331 - 1335
  • [28] 3-ONIUM DERIVATIVES OF 1,4-BENZODIAZEPIN-2-ONES WITH TERTIARY ORGANIC BASES
    KOVAC, T
    KAJFEZ, F
    SUNJIC, V
    OKLOBDZIJA, M
    JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (07) : 766 - 769
  • [29] CONFIGURATIONAL STABILITY OF CHIRAL CENTER C(3) IN SOME 1,4-BENZODIAZEPIN-2-ONES
    SUNJIC, V
    DEJANOVIC, R
    PALKOVIC, A
    KLASINC, L
    KAJFEZ, F
    TETRAHEDRON LETTERS, 1976, (49) : 4493 - 4496
  • [30] Preparation of 3-amino-1,4-benzodiazepin-2-ones via direct azidation with trisyl azide
    Butcher, JW
    Liverton, NJ
    Selnick, HG
    Elliot, JM
    Smith, GR
    Tebben, AJ
    Pribush, DA
    Wai, JS
    Claremon, DA
    TETRAHEDRON LETTERS, 1996, 37 (37) : 6685 - 6688
12345