A novel acylative ring cleavage of benzothieno[3,2-b]pyran-4-ols:: application to the synthesis of dibenzothiophenes and fused-ring derivatives

被引:3
|
作者
Gabbutt, CD [1 ]
Hepworth, JD [1 ]
Heron, BM [1 ]
Thomas, JL [1 ]
机构
[1] Univ Hull, Dept Chem, Hull HU6 7RX, N Humberside, England
关键词
D O I
10.1039/a900730j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The benzothienopyranols 3, readily available from the ketone 1, are transformed to the carbamates 5 on treatment with N,N-dimethylcarbamoyl chloride, subsequent thermal electrocyclisation provides access to dibenzothiophene derivatives 6 and 11-13.
引用
下载
收藏
页码:541 / 542
页数:2
相关论文
共 50 条
  • [21] Oxacycle-Fused [1]Benzothieno[3,2-b][1]benzothiophene Derivatives: Synthesis, Electronic Structure, Electrochemical Properties, Ionisation Potential, and Crystal Structure
    Mohankumar, Meera
    Chattopadhyay, Basab
    Hadji, Rachid
    Sanguinet, Lionel
    Kennedy, Alan R.
    Lemaur, Vincent
    Cornil, Jerome
    Fenwick, Oliver
    Samori, Paolo
    Geerts, Yves
    CHEMPLUSCHEM, 2019, 84 (09): : 1263 - 1269
  • [22] A simple and efficient route to N-functionalized dithieno[3,2-b:2′,3′-d]pyrroles:: Fused-ring building blocks for new conjugated polymeric systems
    Ogawa, K
    Rasmussen, SC
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07): : 2921 - 2928
  • [23] Simple and efficient route to N-functionalized dithieno[3,2-b:2′,3′-d]pyrroles:: Fused-ring building blocks for new conjugated polymeric systems
    Ogawa, K
    Rasmussen, SC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U385 - U385
  • [24] Studies on quinazolines. Part III. Synthesis of some fused-ring cationic and mesoionic derivatives of the 1,3-thiazolo[3,2-c]quinazoline ring system
    Wasfy, AAF
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (09) : 1901 - 1910
  • [25] Domino Knoevenagel hetero-Diels-Alder reactions:: a stereoselective synthesis of sugar fused furo[3,2-b]pyrano[4,3-d]pyran derivatives
    Yadav, JS
    Reddy, BVS
    Narsimhaswamy, D
    Lakshmi, PN
    Narsimulu, K
    Srinivasulu, G
    Kunwar, AC
    TETRAHEDRON LETTERS, 2004, 45 (17) : 3493 - 3497
  • [26] SYNTHESIS AND ANTITUMOR-ACTIVITY OF FUSED QUINOLINE DERIVATIVES .3. NOVEL N-GLYCOSYLAMINOINDOLO[3,2-B]QUINOLINES
    TAKEUCHI, Y
    CHANG, MR
    HASHIGAKI, K
    TASHIRO, T
    TSURUO, T
    TSUKAGOSHI, S
    YAMATO, M
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (06) : 1481 - 1485
  • [27] The formation of the pyridine ring in the synthesis of dipyrido-[3′,2′:4,5]thieno[3,2-b: 3,2-d]pyridines
    V. K. Vasilin
    M. M. Lipunov
    L. D. Konyushkin
    E. A. Kaigorodova
    G. D. Krapivin
    Chemistry of Heterocyclic Compounds, 2006, 42 (10) : 1368 - 1369
  • [28] An efficient star-shaped fused-ring electron acceptor with C3h-symmetric core via thieno[3,2-b]thiophene extending conjugation strategy
    Wang, Weijie
    Wang, Tong
    Wu, Xiaofu
    Tong, Hui
    Wang, Lixiang
    MATERIALS CHEMISTRY FRONTIERS, 2020, 4 (11) : 3328 - 3337
  • [29] A fused-ring non-fullerene acceptor based on a benzo[1,2-b:4,5-b′]dithiophene central core with a thieno[3,2-b]thiophene side-chain for highly efficient organic solar cells
    Jia, Yu
    Zhang, Yun
    Jiang, Wei
    Su, Bin
    Liu, Chunbo
    Zhu, Enwei
    Che, Guangbo
    JOURNAL OF MATERIALS CHEMISTRY A, 2019, 7 (18) : 10905 - 10911
  • [30] Review on Synthesis and Medicinal Application of Dihydropyrano[3,2-b]Pyrans and Spiro-Pyrano[3,2-b]Pyrans by Employing the Reactivity of 5-Hydroxy-2-(Hydroxymethyl)-4H-Pyran-4-One
    Borah, Biplob
    Dwivedi, Kartikey Dhar
    Chowhan, L. Raju
    POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (09) : 5893 - 5937