Chemoselective synthesis of thieno [3,2-c] [1,8]naphthyridin-4(5H-ones by tandem cyclization

被引：5
|
作者：
Majumdar, Krishna C. [1 ]
Rafique-ul-Islam [1 ]
机构：
[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India
来源：
HETEROATOM CHEMISTRY | 2007年 / 18卷 / 01期
关键词：
D O I：
10.1002/hc.20234
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A number of the thieno[3,2-c][1,8]naphthyridin-4(5H)-ones are chemoselectively synthesized from 4-(4'-aryloxybut-2'-ynylthio)-l-phenyl-1,8-naphthyridin-2(1H)-ones in 82-90% yield by the formation of sulfoxide, followed by [2,3] and [3,3]sigmatropic rearrangement and an intramolecular Michael addition. (c) 2007 Wiley Periodicals, Inc.
引用
收藏
页码：87 / 92
页数：6
相关论文
共 50 条
  • [1] A FACILE AND NOVEL SYNTHESIS OF 5-PHENYLIMIDAZO[4,5-C][1,8]NAPHTHYRIDIN-4(5H)-ONES
    KURODA, T
    SUZUKI, F
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (08) : 2029 - 2034
  • [2] NEW BRONCHODILATORS .3. IMIDAZO[4,5-C][1,8]NAPHTHYRIDIN-4(5H)-ONES
    SUZUKI, F
    KURODA, T
    KAWAKITA, T
    MANABE, H
    KITAMURA, S
    OHMORI, K
    ICHIMURA, M
    KASE, H
    ICHIKAWA, S
    JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (26) : 4866 - 4874
  • [3] A new approach to the synthesis of benzo[b][1,8]naphthyridin-4(1H)ones.
    Vijayalakshmi, S
    Ragunath, L
    Rajendran, SP
    HETEROCYCLIC COMMUNICATIONS, 2001, 7 (02) : 177 - 182
  • [4] A FACILE SYNTHESIS OF 5-PHENYLIMIDAZO-[4,5-C][1,8]NAPHTHYRIDIN-4(5H)-ONE
    KUGE, Y
    KATO, N
    SUGAYA, T
    TOMIOKA, S
    SYNTHETIC COMMUNICATIONS, 1994, 24 (22) : 3289 - 3296
  • [5] Tandem cyclization:: one pot regioselective synthesis of thieno[3,2-c]quinolin-4(5H)-one derivatives
    Majumdar, KC
    Ghosh, M
    TETRAHEDRON, 2002, 58 (50) : 10047 - 10052
  • [6] CONDENSED 1,8-NAPHTHYRIDINES .8. SYNTHESIS OF 2-ARYLPYRIMIDO[4,5-B][1,8]NAPHTHYRIDIN-4(3H)-ONES
    REDDY, KR
    MOGILAIAH, K
    SREENIVASULU, B
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1987, 26 (12): : 1194 - 1196
  • [7] SYNTHESIS OF INDOLO[3,2-C]-[1,8]NAPHTYRIDINES
    DASETTIMO, A
    PRIMOFIORE, G
    LATTE, M
    CHIMICA & L INDUSTRIA, 1975, 57 (02): : 135 - 135
  • [8] A New Approach to the Synthesis of Benzo[c][1,7] naphthyridin-4(3H)-ones
    Kulakov, Ivan V.
    Shatsauskas, Anton L.
    Matsukevich, Mariya V.
    Palamarchuk, Irina V.
    Seilkhanov, Tulegen M.
    Gatilov, Yuriy V.
    Fisyuk, Alexander S.
    SYNTHESIS-STUTTGART, 2017, 49 (16): : 3700 - 3709
  • [9] Expedited access to thieno[3,2-c]quinolin-4(5H)ones and benzo[h]-1,6-naphthyridin-5(6H)-ones via a continuous flow photocyclization method
    Fang, Y.
    Tranmer, G. K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (46) : 10799 - 10803
  • [10] SYNTHESIS OF NEW INDOLO[3,2-C][1,8]NAPHTHIRIDINES
    DASETTIMO, A
    BIAGI, G
    PRIMOFIORE, G
    CHIMICA & L INDUSTRIA, 1977, 59 (12): : 877 - 878
12345