DABCO-Promoted Bicyclization/Rearrangement Reaction Synthesis of Tetrasubstituted Furans and Furo[3,4-d]pyrimidine-2,4-diones from 1,4-Enediones

被引:0
作者
Zhang, Wen-Wen [1 ]
Gan, Shao-Ting [1 ]
Qin, Zhao-Yi [1 ]
Jin, Mei [1 ]
Liu, Shan [1 ]
Shu, Wen-Ming [1 ]
Wu, An-Xin [2 ]
机构
[1] Yangtze Univ, Coll Chem & Environm Engn, Hubei Engn Res Ctr Clean Prod & Pollut Control Oil, Jingzhou 434023, Peoples R China
[2] Cent China Normal Univ, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China
基金
中国国家自然科学基金;
关键词
1,4-Enediones; Cyanamide; Polysubstituted furans; Bicyclization; Synthesis; C BOND-CLEAVAGE; 1,3-DICARBONYL COMPOUNDS; EFFICIENT SYNTHESIS; METHYL KETONES; CYCLOADDITION; INTEGRATION; STRATEGY;
D O I
10.1002/ejoc.202300810
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A DABCO-promoted bicyclization/rearrangement reaction has been developed for the synthesis of tetrasubstituted furans from 1,4-enediones at room temperature. This transformation involves aza-Michael addition, intramolecular bicyclization, and rearrangement processes. In addition, the 4-ureidofuran-3-carboxylate ester products can further be converted to furo[3,4-d]pyrimidine-2,4-diones through intramolecular substitution cyclization under heating conditions.
引用
收藏
页数:5
相关论文
共 34 条
  • [1] The total synthesis of (±)-rishirilide B
    Allen, JG
    Danishefsky, SJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (02) : 351 - 352
  • [2] Stereoselective synthesis of (E)-4-alkylidenecyclopent-2-en-1-ones by a tandem ring closure-Michael addition-elimination
    Ballini, R
    Bosica, G
    Fiorini, D
    Gil, MV
    Petrini, M
    [J]. ORGANIC LETTERS, 2001, 3 (09) : 1265 - 1267
  • [3] Solution-Phase Synthesis of a Highly Substituted Furan Library
    Cho, Chul-Hee
    Shi, Feng
    Jung, Dai-Il
    Neuenswander, Benjamin
    Lushington, Gerald H.
    Larockt, Richard C.
    [J]. ACS COMBINATORIAL SCIENCE, 2012, 14 (07) : 403 - 414
  • [4] An Efficient Synthesis of Hydantoins via Sustainable Integration of Coupled Domino Processes
    Gao, Meng
    Yang, Yan
    Wu, Yan-Dong
    Deng, Cong
    Shu, Wen-Ming
    Zhang, Dong-Xue
    Cao, Li-Ping
    She, Neng-Fang
    Wu, An-Xin
    [J]. ORGANIC LETTERS, 2010, 12 (18) : 4026 - 4029
  • [5] Formation of Unsymmetrical 1,4-Enediones via A Focusing Domino Strategy: Cross-Coupling of 1,3-Dicarbonyl Compounds and Methyl Ketones or Terminal Aryl Alkenes
    Gao, Meng
    Yang, Yan
    Wu, Yan-Dong
    Deng, Cong
    Cao, Li-Ping
    Meng, Xiang-Gao
    Wu, An-Xin
    [J]. ORGANIC LETTERS, 2010, 12 (08) : 1856 - 1859
  • [6] Unexpected C-C Bond Cleavage: A Route to 3,6-Diarylpyridazines and 6-Arylpyridazin-3-ones from 1,3-Dicarbonyl Compounds and Methyl Ketones
    Gao, Qinghe
    Zhu, Yanping
    Lian, Mi
    Liu, Meicai
    Yuan, Jingjing
    Yin, Guodong
    Wu, Anxin
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (21) : 9865 - 9870
  • [7] Discovery of furan-2-carbohydrazides as orally active glucagon receptor antagonists
    Hasegawa, Futoshi
    Niidome, Kazumi
    Migihashi, Chiaki
    Murata, Makoto
    Negoro, Toshiyuki
    Matsumoto, Takafumi
    Kato, Kaori
    Fujii, Akihito
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (17) : 4266 - 4270
  • [8] One-Pot Transformation of Simple Furans into 4-Hydroxy-2-cyclopentenones in Water
    Kalaitzakis, Dimitris
    Triantafyllakis, Myron
    Alexopoulou, Ioanna
    Sofiadis, Manolis
    Vassilikogiannakis, Georgios
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (48) : 13201 - 13205
  • [9] Syntheses of polysubstituted furans: recent developments
    Kirsch, SF
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) : 2076 - 2080
  • [10] Synthesis of Tetrasubstituted Furans through One-Pot Formal [3+2] Cycloaddition Utilizing [1,2]-Phospha-Brook Rearrangement
    Kondoh, Azusa
    Aita, Kohei
    Ishikawa, Sho
    Terada, Masahiro
    [J]. ORGANIC LETTERS, 2020, 22 (05) : 2105 - 2110