ONE-POT SYNTHESIS OF 2-SUBSTITUTED 3-THIOXO-2,3-DIHYDRO-1H-ISOINDOL-1-ONES BY THE REACTION OF N-SUBSTITUTED 2,N-DILITHIOBENZAMIDES WITH ISOTHIOCYANATES

被引:4
|
作者
Kobayashi, Kazuhiro [1 ]
Fujiwara, Daiki [1 ]
机构
[1] Tottori Univ, Grad Sch Sustainabil Sci, Dept Engn, Appl Chem Field,Chem & Biotechnol Course, 4-101 Koyama Minami, Tottori 6808552, Japan
关键词
DERIVATIVES; ANTAGONISTS; DESIGN;
D O I
10.3987/COM-17-13756
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper describes an efficient one-pot method for the preparation of 2-substituted 3-thioxo-1H-isoindol-l-ones (3-thioxoisoindolinones) by the reaction of N-substituted 2,N-dilithiobenzamides, generated by treating N-substituted benzamides with two equivalents of butyllithium, with the respective isothiocyanates followed by ring closure of the resulting N-alkyl(or aryl)-2-(alkyl(or aryl)thiocarbamoyl)benzamide derivatives with loss of alkyl(or aryl)amines.
引用
收藏
页码:1759 / 1765
页数:7
相关论文
共 50 条
  • [11] Copper-catalysed one-pot synthesis of N-substituted benzo[d]isothiazol-3(2H)-ones via C-S/N-S bond formation
    Paul, Rajesh
    Punniyamurthy, Tharmalingam
    RSC ADVANCES, 2012, 2 (18) : 7057 - 7060
  • [12] A One-Pot Synthesis of 3-Amino-1H-isoindol-1-one thiazol-2-ylhydrazones
    Biitseva, Angelina
    Groth, Ulrich
    Hordiyenko, Olga
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (05) : 1140 - 1145
  • [13] Hydriodic Acid-Mediated Cyclization of α-Substituted Secondary 2-Ethenylbenzamides: Synthesis of 2-Substituted 2,3-Dihydro-3,3-dimethyl-1H-isoindol-1-ones and 3,3-Disubstituted (E)-1-(Arylimino)-1,3-dihydroisobenzofurans
    Kobayashi, Kazuhiro
    Fujita, Seiki
    Nakai, Daisuke
    Fukumoto, Shogo
    Fukamachi, Shuhei
    Konishi, Hisatoshi
    HELVETICA CHIMICA ACTA, 2010, 93 (07) : 1274 - 1280
  • [14] One-pot synthesis of quinazolin-4(3 H)-ones and 2,3-dihydroquinazolin-4(1 H)-ones utilizing N-(2-aminobenzoyl)benzotriazoles
    Senol, Ilbilge Merve
    Celik, Ilhami
    Avan, Ilker
    TURKISH JOURNAL OF CHEMISTRY, 2019, 43 (06) : 1580 - +
  • [15] Iodine: Selectively Promote the Synthesis of Mono Substituted Quinazolin-4(3H)-ones and 2,3-Dihydroquinazolin-4(1H)-ones in One-Pot
    Zeng, Li-Yan
    Cai, Chun
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (05) : 1035 - 1039
  • [16] One pot cascade synthesis of substituted 1,2,4-triazol-3-ones
    Su YeHua
    Jiang Zhen
    Hong Deng
    Lin XianFu
    Wang YanGuang
    CHINESE SCIENCE BULLETIN, 2010, 55 (25): : 2879 - 2884
  • [17] A Two-Step, One-Pot Enzymatic Synthesis of 2-Substituted 1,3-Diols
    Kalaitzakis, Dimitris
    Smonou, Ioulia
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24) : 8658 - 8661
  • [18] Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines
    Sun, Hongnan
    Huang, Binbin
    Lin, Run
    Yang, Chao
    Xia, Wujiong
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 524 - 529
  • [19] A Simple One-Pot Synthesis of 2-Substituted Quinazolin-4(3H)-ones from 2-Nitrobenzamides by Using Sodium Dithionite
    Romero, Angel H.
    Salazar, Jose
    Lopez, Simon E.
    SYNTHESIS-STUTTGART, 2013, 45 (14): : 2043 - 2050
  • [20] An Efficient One-Pot Strategy for the Synthesis of Triazole-Fused 1,4-Benzodiazepinones from N-Substituted 2-Azidobenzamides
    Majumdar, K. C.
    Ganai, Sintu
    SYNTHESIS-STUTTGART, 2013, 45 (18): : 2619 - 2625