SYNTHESIS OF SOME NEW SPIROHETEROCYCLES RELATED TO SPIRO[INDOLINE-3,2'-[1,3]OXATHIALANE]-2,5'-DIONE

被引：22
|
作者：
ALTHEBEITI, MS [1 ]
ELZOHRY, MF [1 ]
机构：
[1] UNIV ASSIUT,DEPT CHEM,ASSIUT,EGYPT
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1994年 / 88卷 / 1-4期
关键词：
SPIROINDOLINE DERIVATIVES; SPIROHETEROCYCLES; NMR;
D O I：
10.1080/10426509408036929
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The reaction of indole-2,3-dione (1a) and/or 1-methylindole-2,3-dione (1b) with mercaptoacetic acid in the presence of 4-toluenesulfonic acid as a catalyst afforded spiro[indoline-3,2'-[1,3]oxathialane]-2,5'-diones (2a, b). Compounds 2a and/or 2b were reacted with the appropriate aliphatic and/or aromatic primary amines to give compounds 3a-j. The reaction of 2a, b with hydrazine hydrate, phenylhydrazine and p-nitrophenylhydrazine yielded spiroderivatives 4a-c. Friedel-Crafts reactions of 2a and 2b with arenes in the presence of aluminium chloride catalyst afforded spiroindoline isothiochroman derivatives 5a-h.
引用
收藏
页码：251 / 256
页数：6
相关论文
共 50 条
  • [41] Preparation and antiplasmodial activity of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones
    Mathebula, Bakolise
    Butsi, Kamogelo Rosinah
    van Zyl, Robyn Lynne
    van Vuuren, Natasha Colleen Jansen
    Hoppe, Heinrich Carl
    Michael, Joseph Philip
    de Koning, Charles Bernard
    Rousseau, Amanda Louise
    CHEMICAL BIOLOGY & DRUG DESIGN, 2019, 94 (04) : 1849 - 1858
  • [42] Methyl 5''-chloro-1 ',1''-dimethyl-2,2''-dioxodispiro[indoline-3,2 '-pyrrolidine-3 ',3''-indoline]-4 '-carboxylate
    Kannan, Piskala Subburaman
    Yuvaraj, PanneerSelvam
    Manivannan, Karthikeyan
    Reddy, Boreddy Siva Rami
    SubbiahPandi, Arunachalathevar
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O825 - +
  • [43] Concise Synthesis of Spiro[indoline-3,2'-pyrrolidine] and 1-Azacarbazole Derivatives via Copper-Catalyzed Cyclization of Indoles
    Wang, Peng-Fei
    Chen, Chao
    Chen, Hui
    Han, Li-Shuai
    Liu, Liu
    Sun, Hongbin
    Wen, Xiaoan
    Xu, Qing-Long
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (14) : 2339 - 2344
  • [44] SYNTHESIS OF 2,4'-DIOXOSPIRO[INDOLINE-3,2'-THIAZOLIDINE]-5'-ACETIC ACIDS - X-RAY STRUCTURE OF 1-BENZYL-3'-(4-CHLOROPHENYL)-2,4'-DIOXOSPIRO-[INDOLINE-3,2'-THIAZOLIDINE]-5'-ACETIC ACID
    POPP, FD
    RAJOPADHYE, M
    BROWN, DS
    WADDINGTON, D
    UFF, BC
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (01) : 261 - 265
  • [45] Synthesis of novel 2-oxospiro[indoline-3,4′-[1,3]dithiine]-5′-carbonitrile derivatives by new spiro[indoline-3,4′-[1,3]dithiine]@Cu(NO3)2 supported on Fe3O4@gly@CE MNPs as efficient catalyst and evaluation of biological activity
    Moghaddam-Manesh, Mohammadreza
    Sheikhhosseini, Enayatollah
    Ghazanfari, Dadkhoda
    Akhgar, Mohammadreza
    BIOORGANIC CHEMISTRY, 2020, 98
  • [46] Synthesis of 1′-aryl-2′-(2-oxoindolin-3-yl)spiro[indoline-3,5′-pyrroline]-2,3′-dione via one-pot reaction of arylamines, acetone, and isatins
    Sun, Yan
    Sun, Jing
    Yan, Chao-Guo
    TETRAHEDRON LETTERS, 2012, 53 (28) : 3647 - 3649
  • [47] Novel series of dihydroquinolindihydro-spiro[indoline-3,6′-[1,3]thiazine]-5′-carbonitrile derivatives
    Mohamed, Asmaa H.
    Alshammari, Mohammed B.
    El-Sheref, Esmaat M.
    Aly, Ashraf A.
    JOURNAL OF MOLECULAR STRUCTURE, 2020, 1219
  • [48] Facile synthesis of spiro[indoline-3,3′-pyrrolo[1,2-a]quinolines] and spiro-[indoline-3,1′-pyrrolo[2,1-a]isoquinolines] via 1,3-dipolar cycloaddition reactions of heteroaromatic ammonium salts with 3-phenacylideneoxindoles
    Wu, Lei
    Sun, Jing
    Yan, Chao-Guo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (47) : 9452 - 9463
  • [49] A palladium-catalyzed cascade process for spirooxindole: an alternative way for the synthesis of spiro(indoline-3,2′-quinazolin)-2-ones
    Sharma, Abhilash
    Dutta, Dhiraj
    Gogoi, Pranjal
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (08) : 1795 - 1806
  • [50] Novel Functionalized Spiro [Indoline-3,5′-pyrroline]-2,2′dione Derivatives: Synthesis, Characterization, Drug-Likeness, ADME, and Anticancer Potential
    Asif, Mohd
    Alvi, Sahir Sultan
    Azaz, Tazeen
    Khan, Abdul Rahman
    Tiwari, Bhoopendra
    Hafeez, Bilal Bin
    Nasibullah, Malik
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2023, 24 (08)
12345