A Practical, Large-Scale Synthesis of Pyrene-2-Carboxylic Acid

被引:9
|
作者
Casas-Solvas, Juan M. [1 ]
Mooibroek, Tiddo J. [1 ]
Sandramurthy, Shugantan [1 ]
Howgego, Joshua D. [1 ]
Davis, Anthony P. [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
condensed aromatic compounds; electrophilic aromatic substitution; ring closure; ring opening; Haller-Bauer cleavage; 2,7-FUNCTIONALIZED PYRENE DERIVATIVES; POLYCYCLIC AROMATIC-HYDROCARBONS; CARBON NANOTUBES; DNA MODIFICATION; NUCLEIC-ACIDS; HALLER-BAUER; PI-STACKING; CLEAVAGE; PROBES; BORYLATION;
D O I
10.1055/s-0034-1379026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrene-2-carboxylic acid is a versatile intermediate for introducing the unusual 2-pyrenyl unit into functional organic molecules. A classical preparation for this molecule has been revised and improved to give a robust and efficient three-step process. The method has been applied on a multigram scale to give pyrene-2-carboxylic acid in >70% overall yield from pyrene.
引用
收藏
页码:2591 / 2594
页数:4
相关论文
共 50 条
  • [1] PYRENE CHEMISTRY .16. SUBSTITUTES OF PYRENE-2-CARBOXYLIC ACID
    GERASIMENKO, YE
    POTELESH.VP
    ZHURNAL ORGANICHESKOI KHIMII, 1972, 8 (05): : 1074 - +
  • [2] Safe and practical large-scale synthesis of 2-aminoquinoline-6-carboxylic acid benzyl ester
    Couturier, M
    Le, T
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (03) : 534 - 538
  • [3] Practical large-scale synthesis of octalactin A.
    Buszek, KR
    Gibson, TS
    Sato, N
    Jeong, Y
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U100 - U101
  • [4] Practical Large-Scale Preparation of (±)-2-exo-Norbornyl Carboxylic Acid and Its Improved Isolation As the Sodium Salt
    Gu, Jianxin
    Storz, Thomas
    Vyverberg, Frederick
    Wu, Charles
    Varsolona, Richard J.
    Sutherland, Karen
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (04) : 942 - 945
  • [5] Practical large-scale synthesis of monosubstituted anthraquinone derivatives
    Eckenhoff, William T.
    Murphree, S. Shaun
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [6] Development of a Practical Large-Scale Synthesis of Denagliptin Tosylate
    Patterson, Daniel E.
    Powers, Jeremiah D.
    LeBlanc, Michael
    Sharkey, Tyler
    Boehler, Emily
    Irdam, Erwin
    Osterhout, Martin H.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (05) : 900 - 906
  • [7] A PRACTICAL LARGE-SCALE CHEMICAL SYNTHESIS OF CHIRAL GLYCINES
    RAMALINGAM, K
    NANJAPPAN, P
    KALVIN, DM
    WOODWARD, RW
    TETRAHEDRON, 1988, 44 (17) : 5597 - 5604
  • [8] A practical large scale synthesis of 9-(hydroxymethyl)fluorene-4-carboxylic acid (HOFmCO2H)
    Eisenbeis, S
    Phillips, JE
    SYNTHETIC COMMUNICATIONS, 2001, 31 (22) : 3533 - 3536
  • [9] A Practical Synthesis of Indole-2-carboxylic Acid
    Jiang, Ting
    Liu, Ning
    Jiang, Yi-Wen
    Ye, Ping-Ping
    Xu, Wei-Ming
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2017, 49 (05) : 476 - 478
  • [10] Practical large-scale synthesis of cefmatilen, a new cephalosporin antibiotic
    Kobayashi, T
    Masui, Y
    Goto, Y
    Kitaura, Y
    Mizutani, T
    Matsumura, I
    Sugata, Y
    Ide, Y
    Takayama, M
    Takahashi, H
    Okuyama, A
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (05) : 744 - 753