Domino Suzuki coupling and condensation reaction: an efficient strategy towards synthesis of phenanthridines

被引:18
|
作者
Ghosh, Munmun [1 ]
Ahmed, Atiur [1 ]
Singha, Raju [1 ]
Ray, Jayanta K. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India
关键词
Phenanthridine; Domino reaction; Suzuki coupling; N-(2-lodo-aryl)-formamide; Palladium acetate; METAL-FREE; ETHIDIUM-BROMIDE; DERIVATIVES; CYCLIZATION; ANTITUMOR; DNA;
D O I
10.1016/j.tetlet.2014.11.092
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short and convenient hetero-annulation protocol has been developed for the synthesis of substituted phenanthridines via domino Suzuki coupling and condensation between N-(2-iodo-aryl)-formamide derivatives and 2-formylphenylboronic acid in the presence of Pd(OAc)(2), Cs2CO3 and PPh3 as catalytic system in dry DMF at 85-90 degrees C for 6-7 h. The intermediate after Suzuki coupling and deprotection of nitrogen under the same catalytic system, furnishes the corresponding phenanthridines in good yields after immediate condensation and dehydration. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:353 / 355
页数:3
相关论文
共 50 条
  • [21] Facile synthesis of Pd@graphene nanocomposites with enhanced catalytic activity towards Suzuki coupling reaction
    Khan, Mujeeb
    Shaik, Mohammed Rafi
    Adil, Syed Farooq
    Kuniyil, Mufsir
    Ashraf, Muhammad
    Frerichs, Hajo
    Sarif, Massih Ahmad
    Siddiqui, Mohammed Rafiq H.
    Al-Warthan, Abdulrahman
    Labis, Joselito P.
    Islam, Mohammad Shahidul
    Tremel, Wolfgang
    Tahir, Muhammad Nawaz
    [J]. SCIENTIFIC REPORTS, 2020, 10 (01)
  • [22] Sequential and domino Sonogashira coupling:: Efficient tools for the synthesis of diarylalkynes
    Nagy, A
    Novák, Z
    Kotschy, A
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (20) : 4453 - 4461
  • [23] Direct one-pot synthesis of Phenanthrenes via Suzuki-Miyaura coupling/aldol condensation cascade reaction
    Kim, Young Ha
    Lee, Hyuk
    Kim, Yeong Joon
    Kim, Bum Tae
    Heo, Jung-Nyoung
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (02): : 495 - 501
  • [24] Total synthesis of aristolactams via a one-pot suzuki-miyaura coupling/aldol condensation cascade reaction
    Kim, Joa Kyum
    Kim, Young Ha
    Nam, Ho Tae
    Kim, Bum Tae
    Heo, Jung-Nyoung
    [J]. ORGANIC LETTERS, 2008, 10 (16) : 3543 - 3546
  • [25] Efficient synthesis of substituted biaryl anilines and biaryl phenols via a Suzuki cross-coupling reaction
    Liu, B
    Moffett, KK
    Joseph, RW
    Dorsey, BD
    [J]. TETRAHEDRON LETTERS, 2005, 46 (11) : 1779 - 1782
  • [26] Application of Suzuki-Miyaura coupling reaction in the synthesis of salbutamol
    Chen, Liping
    Qiu, Zhongxuan
    Li, Zhenpeng
    Wang, Yuexing
    Huang, Longjiang
    [J]. Jingxi Huagong/Fine Chemicals, 2022, 39 (08): : 1716 - 1721
  • [27] Synthesis of 3-Benzylcoumarins Using Suzuki Coupling Reaction
    Kwon, Young Bum
    Park, JinHyung
    Choi, Bo Ram
    Kim, Hyun Soo
    Yoon, Cheol Min
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (08) : 2897 - 2898
  • [28] Norbornene-Mediated Palladium-Catalysed Domino-Type Catellani Reaction: an Efficient and Regiospecific Acylation/Suzuki Coupling of Aryl Iodides
    Wu, Wenyu
    Yu, Shaopeng
    Gu, Ting
    Fan, Tianyuan
    Zhong, Yue
    Li, Nianguang
    Tang, Yuping
    Jiang, Yi
    Zhu, Xingmei
    Duan, Jinao
    Shi, Zhihao
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (24) : 3075 - 3085
  • [29] A novel convenient approach towards pyrrolo[1,2-b]-pyridazines through a domino coupling-isomerization-condensation reaction
    Wang, Meng
    Tan, Cun
    He, Qian
    Xie, Yuyuan
    Yang, Chunhao
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (16) : 2574 - 2577
  • [30] Efficient Domino Hydroformylation/Benzoin Condensation: Highly Selective Synthesis of α-Hydroxy Ketones
    Dong, Kaiwu
    Sang, Rui
    Soule, Jean-Francois
    Bruneau, Christian
    Franke, Robert
    Jackstell, Ralf
    Beller, Matthias
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (50) : 18033 - 18037