PREPARATION OF SUBSTITUTED DIHYDROFLUORENONES BY PHOTOISOMERIZATION OF BENZOTROPOLONE DERIVATIVES

被引：5
|
作者：
Walter, Brady L. [1 ]
Tabarez, Carlos [2 ]
Cheng, Hiu Yan [1 ]
Moyna, Patrick [2 ]
Moyna, Guillermo [1 ,2 ]
机构：
[1] Univ Sci Philadelphia, Dept Chem & Biochem, Philadelphia, PA 19104 USA
[2] Univ Republica, Fac Quim, Dept Tecnol Quim, Montevideo, Uruguay
来源：
SYNTHETIC COMMUNICATIONS | 2011年 / 41卷 / 19期
基金：
美国国家科学基金会;
关键词：
Benzotropolones; Diels-Alder reaction; photoisomerization; substituted dihydrofluorenones; beta; gamma-unsaturated ketone chromophores; BIOLOGICAL EVALUATION; PHOTOCHEMISTRY; SERIES; DESIGN;
D O I：
10.1080/00397911.2010.515359
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The photoisomerization of the Diels-Alder adduct formed between tetramethylpurpurogallin and maleic anhydride is described. The process is highly stereoselective, involves the beta,gamma-unsaturated ketone chromophore present in the adduct, proceeds through the formation of allyl and aroyl radical intermediates, and leads to a novel substituted dihydrofluorenone in good yields.
引用
收藏
页码：2852 / 2858
页数：7
相关论文
共 50 条
  • [21] Preparation of Ethynylbenzene Derivatives from Substituted Benzaldehydes
    Martynow, Jacek
    Hanselmann, Roger
    Duffy, Erin
    Bhattacharjee, Ashoke
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (05) : 1026 - 1033
  • [22] New method for preparation of α-substituted acrylonitrile derivatives
    N. P. Tsvetkov
    V. E. Vakhmistrov
    A. B. Koldobsky
    V. N. Kalinin
    Russian Chemical Bulletin, 1999, 48 : 1685 - 1687
  • [23] A convenient preparation of β-acetamido substituted tryptamine derivatives
    Boisbrun, M
    Vassileva, E
    Raoul, M
    Laronze, JY
    Sapi, J
    MONATSHEFTE FUR CHEMIE, 2003, 134 (12): : 1641 - 1649
  • [24] PREPARATION OF SUBSTITUTED ISOQUINOLINE DERIVATIVES .2.
    SIMON, L
    TALPAS, G
    PHARMAZIE, 1974, 29 (05): : 314 - 316
  • [25] New method for preparation of α-substituted acrylonitrile derivatives
    Tsvetkov, NP
    Vakhmistrov, VE
    Koldobsky, AB
    Kalinin, VN
    RUSSIAN CHEMICAL BULLETIN, 1999, 48 (09) : 1685 - 1687
  • [26] TROPOLONES .4. THE PREPARATION OF ALPHA-BETA-BENZOTROPOLONE
    COOK, JW
    GIBB, ARM
    RAPHAEL, RA
    SOMERVILLE, AR
    JOURNAL OF THE CHEMICAL SOCIETY, 1952, (FEB): : 603 - 607
  • [27] ON THE PHOTOISOMERIZATION OF THIOPHENE AND THIAZOLE DERIVATIVES
    D'Auria, Maurizio
    Racioppi, Rocco
    HETEROCYCLES, 2009, 78 (03) : 737 - 748
  • [28] PHOTOISOMERIZATION OF AROMATIC DORAMECTIN DERIVATIVES
    SKLAVOUNOS, C
    DEMERS, N
    LUKASZEWICZ, J
    NOWAKOWSKI, M
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1994, 42 (05) : 1228 - 1231
  • [29] PHOTOISOMERIZATION OF 9-SUBSTITUTED VERBENONES
    SHAFFER, GW
    PESARO, M
    JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (17): : 2489 - 2492
  • [30] Photoisomerization of amino substituted dibenzofulvene rotors
    Jayasundara, Udaya K.
    Kim, HyunJong
    Bell, Thomas W.
    Cline, Joseph I.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
12345