On water: catalyst-free chemoselective synthesis of highly functionalized tetrahydroquinazolines from 2-aminophenylacrylate

被引：29
|
作者：
Saunthwal, Rakesh K. [1 ]
Patel, Monika [1 ]
Tiwari, Rakesh K. [2 ]
Parang, Keykavous [2 ]
Verma, Akhilesh K. [1 ]
机构：
[1] Univ Delhi, Dept Chem, Synthet Organ Chem Lab, Delhi 110007, India
[2] Chapman Univ, Coll Pharm, Orange, CA 92866 USA
来源：
GREEN CHEMISTRY | 2015年 / 17卷 / 03期
关键词：
SUPERCRITICAL CARBON-DIOXIDE; TANDEM SYNTHESIS; FLUOROUS MEDIA; ACID-DERIVATIVES; MICHAEL ADDITION; EFFICIENT; 3,4-DIHYDROQUINAZOLINE-2(1H)-THIONES; CYCLIZATION; ALKENES; FACILE;
D O I：
10.1039/c4gc02154a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A green and catalyst-free atom-ecomonic straightforward tandem approach for the synthesis of highly functionalized tetrahydroquinazolines by the reaction of 2-aminophenylacrylates with isothiocyanates using water as an environmentally friendly solvent via amidation and concomitant chemoselective Michael-addition is described.
引用
收藏
页码：1434 / 1441
页数：8
相关论文
共 50 条
  • [31] Catalyst-Free Synthesis of 3-(2-Quinolinemethylene)-Substituted Isoindolinones in Water
    Tian, Youping
    Sun, Jialin
    Zhang, Kaihua
    Li, Gaoqiang
    Xu, Feng
    SYNTHESIS-STUTTGART, 2018, 50 (11): : 2255 - 2265
  • [32] Facile Synthesis of Phosphonates via Catalyst-Free Multicomponent Reactions in Water
    Rostami-Charati, Farmarz
    Hossaini, Zinatossadat
    SYNLETT, 2012, (16) : 2397 - 2399
  • [33] A New, Simple, Catalyst-free Method for the Synthesis of Pyrazolopyranopyrimidines in Magnetized Water
    Bakherad, Mohammad
    Doosti, Rahele
    Keivanloo, Ali
    Gholizadeh, Mostafa
    Amin, Amir H.
    LETTERS IN ORGANIC CHEMISTRY, 2017, 14 (07) : 510 - 516
  • [34] Mild and Catalyst-Free Petasis/Decarboxylative Domino Reaction: Chemoselective Synthesis of N-Benzyl Propargylamines
    Feng, Huangdi
    Jia, Huihui
    Sun, Zhihua
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23): : 11812 - 11818
  • [35] Synthesis of Thioamides by Catalyst-Free Three-Component Reactions in Water
    Xu, Hualong
    Deng, Hang
    Li, Zhengkai
    Xiang, Haifeng
    Zhou, Xiangge
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (31) : 7054 - 7057
  • [36] Catalyst-free direct regiospecific multicomponent synthesis of C3-functionalized pyrroles
    Pawar, Amol Prakash
    Yadav, Jyothi
    Dolas, Atul Jankiram
    Iype, Eldhose
    Rangan, Krishnan
    Kumar, Indresh
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (29) : 5747 - 5758
  • [37] Catalyst-free sulfonylation of activated alkenes for highly efficient synthesis of mono-substituted ethyl sulfones in water
    Yang, Yu
    Tang, Lin
    Zhang, Sheng
    Guo, Xuefeng
    Zha, Zhenggen
    Wang, Zhiyong
    GREEN CHEMISTRY, 2014, 16 (09) : 4106 - 4109
  • [38] A Facile, Mechanochemical, Solvent-, and Catalyst-Free Synthesis of Functionalized 4-Thiazolidinones
    Wahan, Simranpreet K.
    Chawla, Pooja A.
    Singh, Parvesh
    Kumar, Rupesh
    Bhargava, Gaurav
    SYNOPEN, 2023, 07 (04): : 615 - 618
  • [39] Catalyst-Free Chemoselective Synthesis of 3,4-Dihydroquinazoline-2-thiones and 2-Imino[1,3]benzothiazines
    Xie, Ting
    Xiao, Yu
    Zhao, Shuai
    Hu, Xiu-Qin
    Xu, Peng-Fei
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (21): : 10499 - 10505
  • [40] Catalyst-free 1:2 annulation of quinolines with trifluoroacetylacetylenes: an access to functionalized oxazinoquinolines
    Belyaeva, K. V.
    Nikitina, L. P.
    Afonin, A. V.
    Vashchenko, A. V.
    Muzalevskiy, V. M.
    Nenajdenko, V. G.
    Trofimov, B. A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (43) : 8038 - 8041
12345