Ultrasonic-assisted-synthesis of isoindolin-1-one derivatives

被引:10
|
作者
Mardjan, Muhammad Idham Darussalam [1 ]
Hariadi, Muhamad Fadhly [1 ]
Putri, Indah Mutiara [1 ]
Musyarrofah, Nilna Amalia [1 ]
Salimah, Muflihah [1 ]
Purwono, Bambang [1 ]
Commeiras, Laurent [2 ]
机构
[1] Univ Gadjah Mada, Fac Math & Nat Sci, Dept Chem, Bulaksumur POS BLS 21, Yogyakarta 55281, Indonesia
[2] Aix Marseille Univ, iSm2, Cent Marseille, CNRS, F-13013 Marseille, France
关键词
N-ACYL KETIMINES; MULTICOMPONENT REACTION; STRAIGHTFORWARD ACCESS; 3+2 ANNULATION; SONOCHEMISTRY; CHEMISTRY; ALDEHYDES; LACTAMS;
D O I
10.1039/d2ra02720h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A small library of 3-hydroxyisoindolin-1-ones has been prepared from 3-alkylidenephtalides under ultrasonic irradiation. This practical synthesis is featured by group tolerance, high efficiency and yields. The reaction can also be performed in multigram scale and be further extended to access other motifs of isoindolin-1-ones in a one-pot fashion.
引用
收藏
页码:19016 / 19021
页数:6
相关论文
共 50 条
  • [41] Palladium/silver reagent-promoted aryl phosphorylation: flexible synthesis of substituted-3-benzylidene-2-(2-(diphenylphosphoryl)-aryl)-isoindolin-1-one
    Shi, Peng
    Wang, Qing
    Zeng, Xiao
    Zhao, Yingsheng
    Zeng, Runsheng
    RSC ADVANCES, 2017, 7 (85): : 54277 - 54280
  • [42] Synthesis and duplex DNA recognition studies of oligonucleotides containing a ureido isoindolin-1-one homo-N-nucleoside.: A comparison of host-guest and DNA recognition studies
    Mertz, E
    Mattei, S
    Zimmerman, SC
    BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (06) : 1517 - 1526
  • [43] Discovery of potent, orally bioavailable ERK1/2 inhibitors with isoindolin-1-one structure by structure-based drug design
    Ji, Dezhong
    Zhang, Lingzhi
    Zhu, Qihua
    Bai, Ying
    Wu, Yaoyao
    Xu, Yungen
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 164 : 334 - 341
  • [44] Cobalt(II)-Catalyzed Oxidative C-H Alkenylations: Regio- and Site-Selective Access to Isoindolin-1-one
    Ma, Wenbo
    Ackermann, Lutz
    ACS CATALYSIS, 2015, 5 (05): : 2822 - 2825
  • [45] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF POTASSIUM N-METHYLTRIFLUOROBORATE ISOINDOLIN-1-ONE WITH ARYL AND HETEROARYL CHLORIDES
    Nadaf, Rashid N.
    Seapy, Dave G.
    SYNTHETIC COMMUNICATIONS, 2014, 44 (14) : 2012 - 2020
  • [46] 3-Benzyl-4,5,6,7-tetrachloro-3-hydroxy2-(3-hydroxypropyl)isoindolin-1-one
    Fun, Hoong-Kun
    Shen, Yong-Miao
    Xu, Jian-Hua
    Chantrapromma, Suchada
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O944 - O945
  • [47] 2-Difluoroboryl-3-(quinolin-2-ylmethylene)isoindolin-1-one: Efficient Synthesis Method, TD-DFT Analysis and Electrical Properties of Thin Films
    Nabasov, Artem A.
    Koptyaev, Andrey I.
    Usoltsev, Sergey D.
    Rumyantseva, Taisiya A.
    Galanin, Nikolay E.
    MACROHETEROCYCLES, 2022, 15 (02): : 128 - 132
  • [48] Mechanistic insight on water and substrate catalyzed the synthesis of 3-(1H-indol-3-yl)-2-(4-methoxybenzyl)isoindolin-1-one: Driving by noncovalent interactions
    Yuan, Haiyan
    Zhu, Lihan
    Li, Wenliang
    Zhang, Jingping
    JOURNAL OF COMPUTATIONAL CHEMISTRY, 2018, 39 (27) : 2316 - 2323
  • [49] Intramolecular cascade cyclization via photogenerated N-amidyl radicals toward isoindolin-1-one/3,4-dihydroisoquinolin-1(2H)-one fused oxazinane
    He, Yuan-Xiang
    Hu, Kui
    Ran, Yu
    Lei, Zhen-Yao
    Geng, Shu
    Chen, Li-Na
    Pan, Li
    Zhong, Jun-Bo
    Huang, Feng
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (19) : 4871 - 4877
  • [50] AN IMPROVED SYNTHESIS OF [1H]-ISOINDOLIN-1-ONE-3-CARBOXYLIC ACID
    LOWE, JA
    EWING, FE
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (03) : 877 - 877