Synthesis of Dibenzo[b,f]azepines via Palladium-Catalyzed Cascade [4+3] Annulation of o-Alkenyl Bromoarenes and o-Bromoaniline Derivatives

被引：2
|
作者：
Zhan, Xin-Chen [1 ]
Lin, Guo-Qiang [1 ,2 ]
Fu, Jian-Guo [1 ]
Ji, Xiao-Ming [1 ]
Zhang, Shu-Sheng [1 ]
Feng, Chen-Guo [1 ,2 ]
机构：
[1] Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, Res Ctr Chiral Drugs, Shanghai Frontiers Sci Ctr TCM Chem Biol, Shanghai 201203, Peoples R China
[2] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 23期
基金：
中国国家自然科学基金;
关键词：
annulation; dibenzo[b; f]azepines; palladacycle; cascade reaction; palladium; C-H activation; REMOTE METALATION; OXCARBAZEPINE; HETEROCYCLES; ARYL; ARYLATION; BOND;
D O I：
10.1002/adsc.202300336
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A cascade [4+3] annulation of o-alkenyl bromoarenes and o-bromoaniline derivatives was described. Various dibenzo[b,f]azepines with substitutions on the 10/11 position were obtained in 14-97% yields. The synthetic versatility of this protocol is highlighted by the preparation of a precursor of the drug molecule oxcarbazepine, a gram-scale synthesis, and two product transformations. Unlike previous amination/Heck sequence, this cascade process is supposed to undergo a C(vinyl), C(aryl)-palladacycle involved pathway.
引用
收藏
页码：4127 / 4131
页数：5
相关论文
共 50 条
  • [41] Copper-Free Palladium-Catalyzed Sonogashira Coupling-Annulation: Efficient One-Pot Synthesis of Functionalized Pyrano[4,3-b]quinolines from 2-Chloro-3-formylquinolines
    Chandra, Atish
    Singh, Bhawana
    Khanna, Ranjana S.
    Singh, Radhey M.
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) : 5664 - 5666
  • [42] Dibenzo[ b , e ]azepin-6-ones and Seven-Membered Sultam Derivatives: Convenient Synthesis via Palladium-Catalyzed Regioselective Intra-molecular Heck Reaction and Application towards Drug-Like Small Molecules
    Das, Arijit
    Maiti, Arup
    Kundu, Mrinalkanti
    Roy, Kuldeep K.
    Ansary, Inul
    SYNTHESIS-STUTTGART, 2019, 51 (17): : 3231 - 3240
  • [43] Palladium-Catalyzed Oxidative [2+2+1] Annulation of 1,7-Diynes with H2O: Entry to Furo[3,4-c]quinolin-4(5H)-ones
    Ouyang, Xuan-Hui
    Tan, Fang-Lin
    Song, Ren-Jie
    Deng, Wei
    Li, Jin-Heng
    ORGANIC LETTERS, 2018, 20 (21) : 6765 - 6768
  • [44] A palladium-catalyzed cascade approach for the synthesis of 3,3a,4,6,7,8,9,9a-octahydro-1H-benzo[f]isoindole-1,5(2H)-diones
    Cheng, Dong
    Meng, Xiangzhen
    Wang, Dan
    Zhao, Xuan
    Wang, Yusheng
    Ji, Zhiyu
    JOURNAL OF CHEMICAL RESEARCH, 2021, 45 (11-12) : 1107 - 1113
  • [45] Palladium-Catalyzed Intramolecular Migratory Cycloisomerization of 3-Phenoxy Acrylic Acid Ester via C-O Bond Cleavage and C-O/C-C Bonds Formation for 2,3-Disubstituted Benzofurans Synthesis
    Kuboki, Yuichi
    Ohno, Shohei
    Sako, Makoto
    Murai, Kenichi
    Arisawa, Mitsuhiro
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2023, 71 (02) : 93 - 100
  • [46] Regioselective Synthesis of Substituted Imidate N-[1-Methyleneisobenzofuran-3(1H)-ylidene]benzenamines via Palladium-Catalyzed Tandem Heteroannulation of o-(1-Alkynyl)benzamides with Iodobenzene
    Yan, Ze-Yi
    Tan, Cun-Min
    Wang, Xue
    Li, Fei
    Gao, Guo-Lin
    Chen, Xi-Meng
    Wu, Wang-Suo
    Wang, Jian-Jun
    SYNLETT, 2011, (13) : 1863 - 1870
  • [47] Synthesis of 1H-pyrrolo[3,2-c]quinoline derivatives via palladium-catalyzed heteroannulation of 2-aryl-3-iodo-4-(phenylamino)quinolines and 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinolines
    Mphahlele, Malose J.
    Lesenyeho, Lehlohonolo G.
    Makelane, Hlamulo R.
    TETRAHEDRON, 2010, 66 (32) : 6040 - 6046
  • [48] An efficient synthesis of 2H-chromen-3-y1 derivatives via CuI/(NH4)2HPO4 catalyzed reaction of O-propargyl salicylaldehydes with active methylene compounds
    Kumari, Kumkum
    Raghuvanshi, Dushyant Singh
    Singh, Krishna Nand
    TETRAHEDRON, 2013, 69 (01) : 82 - 88
  • [49] Copper- and Palladium-Catalyzed Cross-Coupling Reactions for the Synthesis of N-Fused Benzo[4,5]imidazo[2,1-b]thiazole Derivatives via Substituted trans-1,2-Diiodoalkenes, 1H-Benzo[d]imidazole-2-thiols, and Halobenzenes
    Shen, Guodong
    Yang, Bingchuan
    Huang, Xianqiang
    Hou, Yaxin
    Gao, Huan
    Cui, Jichun
    Cui, Chuansheng
    Zhang, Tongxin
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (07) : 3798 - 3805
  • [50] Synthesis of Substituted Benzo[b]thiophenes via Sequential One-Pot, Copper-Catalyzed Intermolecular C-S Bond Formation and Palladium-Catalyzed Intramolecular Arene-Alkene Coupling of Bis(het)aryl/alkyl-1,3-monothiodiketones and o-Bromoiodoarenes
    Yugandar, Somaraju
    Konda, Saidulu
    Ila, Hiriyakkanavar
    ORGANIC LETTERS, 2017, 19 (07) : 1512 - 1515
12345