Synthesis of tetrahydroquinazolines from 2-aminobenzonitriles and alkylidene malonates via 1,4-conjugate addition and an unprecedented rearrangement reaction

被引:2
作者
Porashar, Bikoshita [1 ]
Behera, Bipin Kumar [1 ]
Phukon, Hunmoina [1 ]
Saikia, Anil K. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Gauhati 781039, Assam, India
关键词
QUINAZOLINONES; DERIVATIVES; AMINATION; EFFICIENT;
D O I
10.1039/d4cc00240g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient methodology for the synthesis of highly diverse tetrahydroquinazoline scaffolds from 2-aminobenzonitriles and alkylidene malonates via 1,4-conjugate addition followed by an unprecedented rearrangement has been demonstrated. The methodology is further applicable for the synthesis of quinazolines and tetracyclic compounds. Some of the synthesized compounds exhibit photophysical properties.
引用
收藏
页码:4358 / 4361
页数:4
相关论文
共 50 条
  • [1] Bioinspired total synthesis of katsumadain A by organocatalytic enantioselective 1,4-conjugate addition
    Wang, Yongguang
    Bao, Ruiyang
    Huang, Shengdian
    Tang, Yefeng
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1601 - 1606
  • [2] Cascade synthesis of quinazolinones from 2-aminobenzonitriles and aryl bromides via palladium-catalyzed carbonylation reaction
    Li, Haoquan
    He, Lin
    Neumann, Helfried
    Beller, Matthias
    Wu, Xiao-Feng
    GREEN CHEMISTRY, 2014, 16 (03) : 1336 - 1343
  • [3] Synthesis of N-Vinyl Nitrones via 1,4-Conjugate Elimination
    Michael, Ryan E.
    Chando, Katelyn M.
    Sammakia, Tarek
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (13) : 6930 - 6935
  • [4] Water enhanced synthesis of gem-bisphosphonates via Rh(I) mediated 1,4-conjugate addition of aryl boronic acids to vinylidenebisphosphonate esters
    Bianchini, Giulio
    Scarso, Alessandro
    Chiminazzo, Andrea
    Sperni, Laura
    Strukul, Giorgio
    GREEN CHEMISTRY, 2013, 15 (03) : 656 - 662
  • [5] Synthesis of arene-functionalized fused heterocyclic scaffolds via a regioselective cascade 1,4-conjugate addition/5-exo-dig annulation strategy
    He, Xinwei
    Wang, Demao
    Liu, Yanan
    Wu, Mengdi
    Kong, Yangzilin
    Tang, Qiang
    Wang, Yiping
    Fan, Chenli
    Shang, Yongjia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (46) : 9159 - 9172
  • [6] Chiral phosphite ligands derived from L-(+)-tartaric acid: synthesis and application in the Cu-catalyzed 1,4-conjugate addition of organozincs to cyclic enones
    Xing, Ai-ping
    Bai, Cai-bing
    Wang, Lai-lai
    TETRAHEDRON, 2013, 69 (02) : 455 - 459
  • [7] Synthesis of β-sulfanyl ketones via a tandem rearrangement-conjugate addition reaction catalyzed by a Re(V)-oxo complex
    Garst, Alyson E.
    Badiceanu, Alexandra D.
    Nolin, Kristine A.
    TETRAHEDRON LETTERS, 2013, 54 (06) : 459 - 461
  • [8] Application of Tertiary Amines Synthesized by Catalytic Dehydrogenation of Enamines as Nucleophilic C2 Synthons for 1,4-Conjugate Addition with Fluoroalkylated Olefins
    Morigaki, Atsunori
    Kawamura, Mio
    Arimitsu, Satoru
    Ishihara, Takashi
    Konno, Tsutomu
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (03) : 239 - 243
  • [9] Visible-Light-Promoted Synthesis of 1,4-Dicarbonyl Compounds via Conjugate Addition of Aroyl Chlorides
    Wang, Chao-Ming
    Song, Dan
    Xia, Peng-Ju
    Wang, Jing
    Xiang, Hao-Yue
    Yang, Hua
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (03) : 271 - 274
  • [10] Synthesis of 1H-Quinazoline-2,4-diones from 2-Aminobenzonitriles by Fixation of Carbon Dioxide with Amidine Moiety Supported Polymer at Atmospheric Pressure
    Nagai, Daisuke
    Endo, Takeshi
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2009, 47 (03) : 653 - 657