Rhodium-catalyzed [2+2+2] cycloaddition reactions of terminal alkynes with N-sulfonyl ketimines

被引:5
|
作者
Zhang, Wei [1 ]
Zhang, Qian-Ru [1 ]
Dong, Lin [1 ]
机构
[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, West China Sch Pharm, Chengdu 610041, Peoples R China
关键词
1,2-Dihydropyridines; Rhodium; Terminal alkynes; 2+2+2] cycloaddition; N-Sulfonyl ketimines; STEREOSELECTIVE-SYNTHESIS; AZA-NICKELACYCLE; IMINES; PYRIDINES; 1,2-DIHYDROPYRIDINES; CYCLIZATION; CHEMISTRY;
D O I
10.1016/j.tetlet.2014.11.122
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple approach for the direct synthesis of 1,2-dihydropyridines was developed involving a one-step rhodium-catalyzed [2+2+2] cycloaddition between N-sulfonyl ketimines and two terminal alkynes. Mechanistic studies suggested a stepwise reaction of an imine and alkyne with rhodium(III), followed by the insertion of a second alkyne. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:546 / 548
页数:3
相关论文
共 50 条
  • [21] Rhodium(I)/cationic 2,2′-bipyridyl-catalyzed [2+2+2] cycloaddition of α,ω-diynes with alkynes in water under air
    Wang, Yun-Hua
    Huang, Shao-Hsien
    Lin, Tze-Chiao
    Tsai, Fu-Yu
    TETRAHEDRON, 2010, 66 (35) : 7136 - 7141
  • [22] Facile Synthesis of Dibenzotetracenedione Derivatives by Rhodium-Catalyzed [2+2+2] Cycloaddition/Spontaneous Aromatization
    Aida, Yukimasa
    Shibata, Yu
    Tanaka, Ken
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (10) : 1823 - 1829
  • [23] Rhodium-NHC Hybrid Silica Materials as Recyclable Catalysts for [2+2+2] Cycloaddition Reactions of Alkynes
    Fernandez, Marti
    Ferre, Meritxell
    Pla-Quintana, Anna
    Parella, Teodor
    Pleixats, Roser
    Roglans, Anna
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (28) : 6242 - 6251
  • [24] Rhodium(I)-Catalyzed Intermolecular [2+2+2] Cycloaddition of Allenyl Aldehydes with Alkynes and Related Cyclization
    Oonishi, Yoshihiro
    Saito, Akira
    Sato, Yoshihiro
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (01) : 81 - 86
  • [25] Rhodium-catalyzed [2+2+2] cycloaddition of various fluorine-containing alkynes-novel synthesis of multi-substituted fluoroalkylated aromatic compounds
    Konno, Tsutomu
    Moriyasu, Kazuki
    Kinugawa, Ryoko
    Ishihara, Takashi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (07) : 1718 - 1724
  • [26] Chiral N-phosphino sulfinamide ligands in rhodium(I)-catalyzed [2+2+2] cycloaddition reactions
    Brun, Sandra
    Parera, Magda
    Pla-Quintana, Anna
    Roglans, Anna
    Leon, Thierry
    Achard, Thierry
    Sola, Jordi
    Verdaguer, Xavier
    Riera, Antoni
    TETRAHEDRON, 2010, 66 (46) : 9032 - 9040
  • [27] Tertiary Carbinamine Synthesis by Rhodium-Catalyzed [3+2] Annulation of N-Unsubstituted Aromatic Ketimines and Alkynes
    Sun, Zhong-Ming
    Chen, Shuo-Ping
    Zhao, Pinjing
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (08) : 2619 - 2627
  • [28] Synthesis of bulky arylphosphanes by rhodium-catalyzed formal [2+2+2] cycloaddition reaction and their use as ligands
    Kobatake, Takayuki
    Kondoh, Azusa
    Yoshida, Suguru
    Yorimitsu, Hideki
    Oshima, Koichiro
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) : 1613 - 1619
  • [29] Selective Aza Diels-Alder and Domino [4+2]/[2+2] Cycloaddition Reactions of Arynes with N-Sulfonyl Ketimines
    Kiran, I. N. Chaithanya
    Reddy, R. Santhosh
    Lagishetti, Chandraiah
    Xu, Huacheng
    Wang, Zhen
    He, Yun
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (03) : 1823 - 1832
  • [30] Synthesis of Pyridylphosphonates by Rhodium-Catalyzed [2+2+2] Cycloaddition of 1,6-and 1,7-Diynes with Diethyl Phosphorocyanidate
    Kashima, Kenichi
    Ishii, Masahiro
    Tanaka, Ken
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (05) : 1092 - 1099