Domino Synthesis of Tetrasubstituted Thiophenes from 1,3-Enynes with Mercaptoacetaldehyde

被引:46
作者
Bharathiraja, Ganesan [1 ]
Sathishkannan, Gopal [1 ]
Punniyamurthy, Tharmalingam [1 ]
机构
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India
关键词
ADENOSINE A(1) RECEPTOR; ONE-POT SYNTHESIS; SUBSTITUTED THIOPHENES; DERIVATIVES; CYCLIZATION; PYRROLES; PRECURSORS; MODULATORS; INHIBITORS; DESIGN;
D O I
10.1021/acs.joc.6b00231
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Domino synthesis of tetrasubstituted thiophenes is described from 1,3-enynes and mercapto-acetaldehyde using DABCO at room temperature via a Michael addition, 5-exo-dig carboannulation, and oxidation sequence under air. The broad substrate scope and mild reaction conditions are significant practical features.
引用
收藏
页码:2670 / 2674
页数:5
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共 39 条
  • [1] Domino metal-free allene-β-lactam-based access to functionalized pyrroles
    Alcaide, Benito
    Almendros, Pedro
    Redondo, Maria C.
    [J]. CHEMICAL COMMUNICATIONS, 2006, (24) : 2616 - 2618
  • [2] Organic semiconductors for solution-processable field-effect transistors (OFETs)
    Allard, Sybille
    Forster, Michael
    Souharce, Benjamin
    Thiem, Heiko
    Scherf, Ullrich
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) : 4070 - 4098
  • [3] Allosteric Modulators of the Adenosine A1 Receptor: Synthesis and Pharmacological Evaluation of 4-Substituted 2-Amino-3-benzoylthiophenes
    Aurelio, Luigi
    Valant, Celine
    Flynn, Bernard L.
    Sexton, Patrick M.
    Christopoulos, Arthur
    Scammells, Peter J.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (14) : 4543 - 4547
  • [4] Expedient synthesis of tetrasubstituted pyrroles via a copper-catalyzed cascade inter-/intramolecular cyclization of 1,3-enynes carry a nitro group with amines
    Bharathiraja, Ganesan
    Sengoden, Mani
    Kannan, Masanam
    Punniyamurthy, Tharmalingam
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (09) : 2786 - 2792
  • [5] A Novel Tandem Sequence to Pyrrole Syntheses by 5-endo-dig Cyclization of 1,3-Enynes with Amines
    Bharathiraja, Ganesan
    Sakthivel, Sekarpandi
    Sengoden, Mani
    Punniyamurthy, Tharmalingam
    [J]. ORGANIC LETTERS, 2013, 15 (19) : 4996 - 4999
  • [6] Substituted 2-Aminothiopen-derivatives: A potential new class of GluR6-Antagonists
    Briel, D.
    Rybak, A.
    Kronbach, C.
    Unverferth, K.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (01) : 69 - 77
  • [7] Synthesis of 1,3-diaryl-1H-benzo[g]indazoles
    Chang, Meng-Yang
    Tai, Hang-Yi
    Chen, Yeh-Long
    Hsu, Ru-Ting
    [J]. TETRAHEDRON, 2012, 68 (38) : 7941 - 7948
  • [8] α,α′-N-Boc-Substituted Bi- and Terthiophenes: Fluorescent Precursors for Functional Materials
    Dong, Yanmei
    Navarathne, Daminda
    Bolduc, Andreanne
    McGregor, Nicholas
    Skene, W. G.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (12) : 5429 - 5433
  • [9] An Atom-Economic Route to Thiophenes and 2,2′-Bithiophenes by Intramolecular Transannulation of gem-Dialkylthio Enynes
    Fang, Guichun
    Li, Jichun
    Wang, Yeming
    Gou, Mingyu
    Liu, Qun
    Li, Xingqi
    Bi, Xihe
    [J]. ORGANIC LETTERS, 2013, 15 (16) : 4126 - 4129
  • [10] gem-Dialkylthio vinylallenes: alkylthio-regulated reactivity and application in the divergent synthesis of pyrroles and thiophenes
    Fang, Zhongxue
    Yuan, Haiyan
    Liu, Ying
    Tong, Zixun
    Li, Huiqin
    Yang, Jin
    Barry, Badru-Deen
    Liu, Jianquan
    Liao, Peiqiu
    Zhang, Jingping
    Liu, Qun
    Bi, Xihe
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (70) : 8802 - 8804