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
  • [31] SYNTHESIS OF N-SUBSTITUTED 3-PYRROLIN-2-ONES
    CHALCHAT, JC
    GARRY, RP
    MICHET, A
    COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II, 1982, 295 (10): : 871 - 873
  • [32] A new and versatile synthetic route to 2-dimethylamino-3-alkyl and arylmethylene-2,3-dihydro-1H-isoindol-1-ones
    Deniau, E
    Enders, D
    TETRAHEDRON LETTERS, 2002, 43 (45) : 8055 - 8058
  • [33] One-pot reaction for the synthesis of N-substituted 2-aminobenzoxazoles using triphenylbismuth dichloride as cyclodesulfurization reagent
    Murata, Yuki
    Matsumoto, Natsuho
    Miyata, Maya
    Kitamura, Yuki
    Kakusawa, Naoki
    Matsumura, Mio
    Yasuike, Shuji
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 859 : 18 - 23
  • [34] A Green, One-Pot Synthesis of Substituted 2,3-Dihydroquinazoline-4(1H)-ones in the Presence of N-Sulfonic Acid Pyridinium Chloride
    Azimi, Seyedeh Bahareh
    Azizian, Javad
    SYNLETT, 2016, 27 (12) : 1836 - 1839
  • [35] One pot solid phase synthesis of 2-substituted 2,3-dihydropyridin-4(1H)-ones on Rinkamide-resin
    Sax, M
    Berning, S
    Wünsch, B
    TETRAHEDRON, 2005, 61 (01) : 205 - 211
  • [36] AN IMPROVED ONE-POT METHOD FOR THE PREPARATION OF 2-SUBSTITUTED 1H-PERIMIDINES
    MAQUESTIAU, A
    BERTE, L
    MAYENCE, A
    VANDENEYNDE, JJ
    SYNTHETIC COMMUNICATIONS, 1991, 21 (21) : 2171 - 2180
  • [37] A One-Pot, Four-Component Synthesis of N-Substituted 2,4-Diarylimidazoles
    Adib, Mehdi
    Ansari, Samira
    Feizi, Shahzad
    Damavandi, Jafar Asgarian
    Mirzaei, Peiman
    SYNLETT, 2009, (20) : 3263 - 3266
  • [38] One-pot synthesis of N-substituted 2,4-thiazolidinediones and computational investigation of the products
    Sakineh Asghari
    Mina Haghdadi
    Savia Momeni Ahangar
    Samaneh Ramezani
    Monatshefte für Chemie - Chemical Monthly, 2013, 144 : 337 - 343
  • [39] One-pot synthesis of N-substituted 2,4-thiazolidinediones and computational investigation of the products
    Asghari, Sakineh
    Haghdadi, Mina
    Ahangar, Savia Momeni
    Ramezani, Samaneh
    MONATSHEFTE FUR CHEMIE, 2013, 144 (03): : 337 - 343
  • [40] Cobalt-catalyzed carbonylation of N-alkylbenzaldimines to 'N-alkylphthalimidines' (=2,3-dihydro-1H-isoindol-1-ones) via tandem C-H activation and cyclocarbonylation
    Funk, Jeffrey K.
    Yennawar, Hemant
    Sen, Ayusman
    HELVETICA CHIMICA ACTA, 2006, 89 (08) : 1687 - 1695