A very short and efficient palladium-catalyzed access to the 3,4-dihydro-2H-1,4-benzoxazine structure

被引：2
|
作者：
Dominczak, Norbert
Lhoste, Paul
Kryczka, Boguslaw
Sinou, Denis
机构：
[1] Univ Lyon 1, CPE Lyon, Lab Synth Asymetr, CNRS,UMR 5181, F-69622 Villeurbanne, France
[2] Univ Lodz, Dept Organ & Appl Chem, PL-90136 Lodz, Poland
来源：
LETTERS IN ORGANIC CHEMISTRY | 2006年 / 3卷 / 05期
关键词：
3,4-dihydro-benzoxazine; palladium; annulation;
D O I：
10.2174/157017806776611935
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium(0)-catalyzed annulation of N-substituted-2-aminophenols with propargylic methyl carbonates afforded the corresponding 3,4-dihydro-2-alkylidene- and 3,4-dihydro-3-alkylidene-2H-benzo[b] [1,4]oxazines; a judicious choice of the substituent at nitrogen allowed the preparation of one of the regioisomers.
引用
收藏
页码：371 / 373
页数：3
相关论文
共 50 条
  • [31] Assembly of 1,3-Dihydro-2H-3-benzazepin-2-one Conjugates via Ugi Four-Component Reaction and Palladium-Catalyzed Hydroamidation
    Wu, Jinlong
    Jiang, Yong
    Dai, Wei-Min
    SYNLETT, 2009, (07) : 1162 - 1166
  • [32] Palladium-Catalyzed Silylcyanation of Ynamides: Regio- and Stereoselective Access to Tetrasubstituted 3-Silyl-2-Aminoacrylonitriles
    Hansjacob, Pierre
    Leroux, Frederic R.
    Gandon, Vincent
    Donnard, Morgan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (14)
  • [33] Palladium-catalyzed double C-H functionalization of 2-aryl-1,3-dicarbonyl compounds: a facile access to alkenylated benzopyrans
    Choppakatla, Subrahmanyam
    Dachepally, Aravind Kumar
    Bollikolla, Had Babu
    TETRAHEDRON LETTERS, 2016, 57 (23) : 2488 - 2491
  • [34] Palladium-Catalyzed Reductive [5+1] Cycloaddition of 3-Acetoxy-1,4-enynes with CO: Access to Phenols Enabled by Hydrosilanes
    Wu, Li-Jun
    Song, Ren-Jie
    Luo, Shenglian
    Li, Jin-Heng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (40) : 13308 - 13312
  • [35] Palladium-Catalyzed Selective Aryl Ring C-H Activation of N-Acyl-2-aminobiaryls: Efficient Access to Multiaryl-Substituted Naphthalenes
    Annamalai, Pratheepkumar
    Chen, Wu-Yin
    Raju, Selvam
    Hsu, Kou-Chi
    Upadhyay, Nitinkumar Satyadev
    Cheng, Chien-Hong
    Chuang, Shih-Ching
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (22) : 3642 - 3648
  • [36] Palladium-Catalyzed Desulfitative Arylation of 5-Alkoxy-3,4-dibromo-2(5H)-furanone with Sodium Arylsulfinates
    Shi, Jie
    Tang, Xiao-Dong
    Wu, Yan-Cheng
    Li, Hua-Nv
    Song, Liu-Juan
    Wang, Zhao-Yang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (06) : 1193 - 1197
  • [37] Synthesis of 3,4-dihydroisoquinoline N-oxides via palladium-catalyzed intramolecular cyclization of 2-alkylbenzaldoximes
    Song, Zhi Y.
    Luo, Jiang
    Ren, De Z.
    Fu, Jun
    Liu, Yun J.
    Jin, Fang M.
    Huo, Zhi B.
    ARKIVOC, 2017, : 148 - 158
  • [38] Palladium-Catalyzed C(sp2)-H Activation for the Formation of C-N Bonds: Rapid Access to Benzimidazoquinazolines
    Guo, Xiaolong
    Hu, Jing
    Zhang, Mengmeng
    Wang, Luyao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (03) : 417 - 421
  • [39] Expeditious synthesis of 3,4-dihydro-2H-1λ6-benzo[e][1,2]thiazine 1,1-dioxides
    Takeuchi, Y
    Liu, ZP
    Satoh, A
    Shiragami, T
    Shibata, N
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1999, 47 (12) : 1730 - 1733
  • [40] One Pot Access to 2′-Aryl-2,3′-Bithiophenes via Twofold Palladium-Catalyzed C-X/C-H Coupling Associated to a Pd-1,4-Migration
    Liu, Linhao
    Doucet, Henri
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (16) : 2783 - 2795
12345