Umpolung of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienones for the regiodivergent synthesis of disubstituted catechols

被引：0
|
作者：
Akazawa, Ryunosuke [1 ]
Mohamed, Ahmed A. B. [1 ,2 ]
Yahata, Kenzo [1 ]
Miyagaki, Kohei [1 ]
Togami, Masaki [1 ]
Sawama, Yoshinari [1 ]
Kanomata, Kyohei [1 ]
Akai, Shuji [1 ]
机构：
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
[2] Mansoura Univ, Fac Pharm, Dept Med Chem, Mansoura 35516, Dakahlia, Egypt
来源：
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2024年 / 97卷 / 11期
关键词：
catechols; hypervalent iodine reagent; rearrangement; POLYCYCLIC AROMATIC-HYDROCARBONS; DERIVATIVES; QUINONES;
D O I：
10.1093/bulcsj/uoae111
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The umpolung of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienones 1 with PhI(OCOCF3)(2) achieved the migration into the more electron-rich C3 position, providing exclusively 3,4-disubstituted catechols 3. Acid-induced rearrangement of 1 produced 4,5-disubstituted catechols 2. These two reactions enabled the highly selective production of two regioisomers of disubstituted catechols, especially biaryls containing catechol moieties, from the common intermediates 1.
引用
收藏
页数：6
相关论文
共 50 条
  • [31] SYNTHESES OF 2-DIALKYLAMINO-4,4-DISUBSTITUTED 5(H-4)-THIAZOLONES
    KOBAYASHI, A
    UMEMOTO, S
    KATO, M
    YAKUGAKU ZASSHI, 1970, 90 (11): : 1377 - +
  • [32] SYNTHESIS OF 4,4-DISUBSTITUTED 1,3-THIAZOL-5(4H)-THIONES
    JENNY, C
    HEIMGARTNER, H
    HELVETICA CHIMICA ACTA, 1986, 69 (02) : 374 - 388
  • [33] Solvent-free microwave-assisted efficient synthesis of 4,4-disubstituted 2-oxazolines
    García-Tellado, F
    Loupy, A
    Petit, A
    Marrero-Terrero, AL
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) : 4387 - 4391
  • [34] Diastereocontrolled synthesis of an enantiopure 4,4-disubstituted cyclohex-2-en-ol: a new route to (+)-quebrachamine
    Fujimura, T
    Nakashima, H
    Sakagami, H
    Taniguchi, T
    Ogasawara, K
    TETRAHEDRON LETTERS, 2002, 43 (01) : 97 - 99
  • [35] Synthesis of 4,4-disubstituted 2-aminocyclopentanecarboxylic acid derivatives and their incorporation into 12-helical β-peptides
    Peelen, TJ
    Chi, YG
    English, EP
    Gellman, SH
    ORGANIC LETTERS, 2004, 6 (24) : 4411 - 4414
  • [36] THE SYNTHESIS OF SOME 4,4'-DISUBSTITUTED 2,2'-BIPYRIDINES
    MAERKER, G
    CASE, FH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (11) : 2745 - 2748
  • [37] Selective synthesis of 2,5-disubstituted furan-3-carboxylates and the isomeric 2,4-disubstituted furan-3-carboxylates
    Chen, Panpan
    Meng, Yinggao
    Yang, Qinghua
    Wu, Jie
    Xiao, Yuanyuan
    Gorja, Dhilli Rao
    Song, Chuanjun
    Chang, Junbiao
    RSC ADVANCES, 2015, 5 (97) : 79906 - 79914
  • [38] EFFECT OF COORDINATION WITH RHODIUM ON THE SELECTIVITY OF THE MASS-SPECTRAL FRAGMENTATION OF 4,4-DISUBSTITUTED 2,5-CYCLOHEXADIEN-1-ONES
    ZAGOREVSKII, DV
    NIKANOROV, VA
    GINZBURG, BI
    ROZENBERG, VI
    NEKRASOV, YS
    KAVERIN, VV
    YUREV, VP
    REUTOV, OA
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1986, 35 (05): : 984 - 989
  • [39] A novel synthesis of 2,5-disubstituted 1,3,4-oxadiazolines by the regioselective cyclization of 1,4-disubstituted thiosemicarbazides
    Feng, Dexin
    Huang, You
    Chen, Ruyu
    Yu, Yaqin
    Song, Haibin
    SYNTHESIS-STUTTGART, 2007, 12 (12): : 1779 - 1784
  • [40] Improved synthesis of 4,4-disubstituted-2-aminomethyl oxetanes
    Lian, Huawen
    Liu, GuiHua
    Yu, ShanBao
    Yang, Minmin
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
12345