I2-mediated coupling of quinazolinone enamines with 2-aminopyridines: a new strategy to access spiroquinazolinones

被引:13
作者
Fang, Jingxi
Pan, Zhentao [1 ]
Liu, Tong
Rao, Yingbo
Jiang, Huajiang
Ma, Yongmin [1 ]
机构
[1] Taizhou Univ, Inst Adv Studies, Jiaojiang 318000, Zhejiang, Peoples R China
关键词
SELECTIVE PDE7 INHIBITORS; ALPHA-ALKYLATION; UMPOLUNG; ORGANOCATALYSIS; DERIVATIVES; CYCLOADDITION; ACTIVATION; REACTIVITY; ALDEHYDES; PROTOCOL;
D O I
10.1039/d3ob00083d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report a novel, rapid and efficient route to the spiroquinazolinone framework via an umpolung strategy mediated by molecular iodine. A library of functionalized spiroquinazolinone iodide salts was synthesized in moderate to good yields under ambient, metal-free and mild conditions. The current methodology opens up a new efficient and concise strategy for the construction of spiroquinazolinones.
引用
收藏
页码:2355 / 2360
页数:6
相关论文
共 61 条
  • [1] An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung
    Bauer, Adriano
    Di Mauro, Giovanni
    Li, Jing
    Maulide, Nuno
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (41) : 18208 - 18212
  • [2] Enantioselective organocatalysis using SOMO activation
    Beeson, Teresa D.
    Mastracchio, Anthony
    Hong, Jun-Bae
    Ashton, Kate
    MacMillan, David W. C.
    [J]. SCIENCE, 2007, 316 (5824) : 582 - 585
  • [3] Spiroquinazolinones as novel, potent, and selective PDE7 inhibitors. Part 2: Optimization of 5,8-disubstituted derivatives
    Bernardelli, P
    Lorthiois, E
    Vergne, F
    Oliveira, C
    Mafroud, AK
    Proust, E
    Pham, N
    Ducrot, P
    Moreau, F
    Idrissi, M
    Tertre, A
    Bertin, B
    Coupe, M
    Chevalier, E
    Descours, A
    Berlioz-Seux, F
    Berna, P
    Li, M
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (18) : 4627 - 4631
  • [4] Novel 7-methoxy-6-oxazol-5-yl-2,3-dihydro-1H-quinazolin-4-ones as IMPDH inhibitors
    Birch, HL
    Buckley, GM
    Davies, N
    Dyke, HJ
    Frost, EJ
    Gilbert, PJ
    Hannah, DR
    Haughan, AF
    Madigan, MJ
    Morgan, T
    Pitt, WR
    Ratcliffe, AJ
    Ray, NC
    Richard, MD
    Sharpe, A
    Taylor, AJ
    Whitworth, JM
    Williams, SC
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (23) : 5335 - 5339
  • [5] Aldehyde N,N-dialkylhydrazones as neutral acyl anion equivalents:: Umpolung of the imine reactivity
    Brehme, Rainer
    Enders, Dieter
    Fernandez, Rosario
    Lassaletta, Jose M.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (34) : 5629 - 5660
  • [6] Organocatalytic umpolung: N-heterocyclic carbenes and beyond
    Bugaut, Xavier
    Glorius, Frank
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3511 - 3522
  • [7] Activation of Chiral (Salen)TiCl2 Complex by Phosphorane for the Highly Enantioselective Cyanation of Nitroolefins
    Chen, Chen
    Wu, Wen-Biao
    Li, Yan-Hong
    Zhao, Qiu-Hua
    Yu, Jin-Sheng
    Zhou, Jian
    [J]. ORGANIC LETTERS, 2020, 22 (05) : 2099 - 2104
  • [8] Tandem β-Alkylation-α-Arylation of Amines by Carbolithiation and Rearrangement of N-Carbamoyl Enamines (Vinyl Ureas)
    Clayden, Jonathan
    Donnard, Morgan
    Lefranc, Julien
    Minassi, Alberto
    Tetlow, Daniel J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (19) : 6624 - +
  • [9] Enantioselective Intramolecular Aldehyde α-Alkylation with Simple Olefins: Direct Access to Homo-Ene Products
    Comito, Robert J.
    Finelli, Femanda G.
    MacMillan, David W. C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (25) : 9358 - 9361
  • [10] Stereoelectronic properties of spiroquinazolinones in differential PDE7 inhibitory activity
    Daga, Pankaj R.
    Doerksen, Robert J.
    [J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 2008, 29 (12) : 1945 - 1954