An Efficient Methodology for the Synthesis of 3-Styryl Coumarins

被引:18
|
作者
Martins, Sergio M. A. [1 ]
Branco, Paula C. S. [2 ]
Pereira, Antonio M. D. R. L. [1 ]
机构
[1] Univ Evora, Dept Quim, Ctr Quim, P-7000671 Evora, Portugal
[2] Univ Nova Lisboa, Fac Ciencias & Tecnol, Dept Quim, REQUIMTE, P-2829516 Caparica, Portugal
关键词
3-vinyl coumarin; 3-styryl coumarin; Heck reaction; palladium; fluorescent dyes; HIGHLY EFFICIENT; BIOLOGICAL EVALUATION; DERIVATIVES; DYES; ION; INHIBITION; POTENT; SENSOR;
D O I
10.1590/S0103-50532012000400014
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Regioselective and highly efficient Heck arylation of 3-vinyl-6,7-dimethoxycoumarin has been developed to afford 3-styryl coumarins in good to very high yields. The increase in conjugation reflects on the absorbance of the synthesized compounds revealing all pronounced bathochromic shifts and hyperchromic effects.
引用
收藏
页码:688 / 693
页数:6
相关论文
共 50 条
  • [1] Convenient Synthesis of 3-Vinyl and 3-Styryl Coumarins
    Gordo, Joana
    Avo, Joao
    Parola, A. Jorge
    Lima, Joao C.
    Pereira, Antonio
    Branco, Paula S.
    ORGANIC LETTERS, 2011, 13 (19) : 5112 - 5115
  • [2] New Methodology for the Synthesis of 3-Substituted Coumarins via Palladium-Catalyzed Site-Selective Cross-Coupling Reactions
    Martins, Sergio
    Branco, Paula S.
    de la Torre, Maria C.
    Sierra, Miguel A.
    Pereira, Antonio
    SYNLETT, 2010, (19) : 2918 - 2922
  • [3] Regioselective C3Alkylation of Indoles for the Synthesis of Bis(indolyl)methanes and 3-Styryl Indoles
    Zhang, Ruiqin
    Ma, Renchao
    Chen, Rener
    Wang, Lei
    Ma, Yongmin
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (03) : 1846 - 1857
  • [4] Dehydrogenative Photocyclization of 3-Styryl Indoles to Fused Indole Systems
    Taskesenligil, Yunus
    Saracoglu, Nurullah
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (23) : 17447 - 17452
  • [5] Efficient and General Synthesis of 3-Aryl Coumarins Using Cyanuric Chloride
    Sashidhara, Koneni V.
    Palnati, Gopala Reddy
    Avula, Srinivasa Rao
    Kumar, Abdhesh
    SYNLETT, 2012, (04) : 611 - 621
  • [6] Efficient Synthesis of 3-Aroyl Coumarins in Water via Catalytic Carbopalladation of Nitriles
    Weng, Yiyi
    Yang, Ting
    Chen, Hantao
    Chen, Zhuo
    Zhu, Meijie
    Zhan, Xuecheng
    CHEMISTRYSELECT, 2019, 4 (48): : 14233 - 14236
  • [7] New Synthesis of (Z)- and (E)-3-Styryl-4-quinolones
    Seixas, Raquel S. G. R.
    Silva, Artur M. S.
    Cavaleiro, Jose A. S.
    SYNLETT, 2010, (15) : 2257 - 2262
  • [8] Improved Synthesis of 3-(Aminoaryl)coumarins
    Joao Matos, Maria
    Gaspar, Alexandra
    Borges, Fernanda
    Uriarte, Eugenio
    Santana, Lourdes
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2012, 44 (06) : 522 - 526
  • [9] Ammonium Metavanadate: A Mild and Efficient Catalyst for the Synthesis of Coumarins
    Mandhane, Priyanka G.
    Joshi, Ratnadeep S.
    Ghawalkar, Anant R.
    Jadhav, Ganesh R.
    Gill, Charansingh H.
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (12): : 2969 - 2972
  • [10] An efficient synthesis of some new 3-bipyridinyl substituted coumarins as potent antimicrobial agents
    Lad, Hemali B.
    Giri, Rakesh R.
    Brahmbhatt, D. I.
    CHINESE CHEMICAL LETTERS, 2013, 24 (03) : 227 - 229