New efficient synthesis of isoquinoline-1,3(2H,4H)-diones and isoindolin-1-ones via sequential Ugi/cyclization reaction

被引：23

作者：

Yuan, Ding ^{[1
]}

Duan, Zhuan ^{[1
]}

Rao, Yong ^{[1
]}

Ding, Ming -Wu ^{[1
]}

机构：

[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China

来源：

TETRAHEDRON | 2016年 / 72卷 / 02期

基金：

中国国家自然科学基金;

关键词：

Isoquinoline-1,3(2H,4H)-dione; Isoindolin-1-one; Ugi reaction; Base catalyzed reaction; Acid catalyst; ONE-POT SYNTHESIS; SELECTIVE INHIBITORS; BETA-LACTAMS; UGI; TANDEM; 3-COMPONENT; ACCESS;

D O I：

10.1016/j.tet.2015.11.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new efficient synthesis of isoquinoline-1,3(2H,4H)-diones or isoindolin-1-ones via sequential Ugi-4CR or Ugi-3CR/cyclization reaction was developed. alpha-Acylamino amides 5, obtained from Ugi-4CR of methyl 2-formylbenzoate, amines, isocyanates and acids, cyclized to give isoquinoline-1,3(2H,4H)-diones 6 in good yields in the presence of catalytic amount of sodium ethoxide. Ugi-3CR of methyl 2-formylbenzoate, amines and isocyanates in the presence of catalytic amount of H3PO4 produced isoindolin-1-ones 7 directly in one-pot fashion. (C) 2015 Elsevier Ltd. All rights reserved.

引用

收藏

页码：338 / 346

页数：9

相关论文

共 40 条

[1] A one-pot, three-component and solvent-free synthesis of 2,3-disubstituted isoindolin-1-ones [J].

Adib, Mehdi ;

Peytam, Fariba ;

Zainali, Mohsen ;

Zhu, Long-Guan ;

Wu, Jing .

TETRAHEDRON LETTERS, 2015, 56 (33) :4729-4732

[2] Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones from 2-formylbenzoic acid [J].

Angel Reyes-Gonzalez, Miguel ;

Zamudio-Medina, Angel ;

Ordonez, Mario .

TETRAHEDRON LETTERS, 2012, 53 (43) :5756-5758

[3]

[Anonymous], 2010, CHEM REV, V110, P1

[4] Electrochemically Initiated Tandem and Sequential Conjugate Addition Processes: One-Pot Synthesis of Diverse Functionalized Isoindolinones [J].

Antico, Pasqualmorica ;

Capaccio, Vito ;

Di Mola, Antonia ;

Massa, Antonio ;

Palombi, Laura .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (09) :1717-1724

[5] Molecular basis of peripheral vs central benzodiazepine receptor selectivity in a new class of peripheral benzodiazepine receptor ligands related to alpidem [J].

Anzini, M ;

Cappelli, A ;

Vomero, S ;

Giorgi, G ;

Langer, T ;

Bruni, G ;

Romeo, MR ;

Basile, AS .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (21) :4275-4284

[6] Densely functionalized 1,2-dihydrobenzo[b] [1,6]naphthyridines: one-pot synthesis via sequential Ugi and Heck reactions [J].

Asthana, Mrityunjaya ;

Sharma, Neha ;

Singh, Radhey M. .

TETRAHEDRON, 2014, 70 (43) :7996-8003

[7] Magnesium Chelating 2-Hydroxyisoquinoline-1,3(2H,4H)-diones, as Inhibitors of HIV-1 Integrase and/or the HIV-1 Reverse Transcriptase Ribonuclease H Domain: Discovery of a Novel Selective Inhibitor of the Ribonuclease H Function [J].

Billamboz, Muriel ;

Bailly, Fabrice ;

Lion, Cedric ;

Touati, Nadia ;

Vezin, Herve ;

Calmels, Christina ;

Andreola, Marie-Line ;

Christ, Frauke ;

Debyser, Zeger ;

Cotelle, Philippe .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (06) :1812-1824

[8] 2-Hydroxyisoquinoline-1,3(2H,4H)-diones as inhibitors of HIV-1 integrase and reverse transcriptase RNase H domain: Influence of the alkylation of position 4 [J].

Billamboz, Muriel ;

Bailly, Fabrice ;

Lion, Cedric ;

Calmels, Christina ;

Andreola, Marie-Line ;

Witvrouw, Myriam ;

Christ, Frauke ;

Debyser, Zeger ;

De Luca, Laura ;

Chimirri, Alba ;

Cotelle, Philippe .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (02) :535-546

[9] Synthesis and antimicrobial activity of some isoindolin-1-ones derivatives [J].

Breytenbach, JC ;

van Dyk, S ;

van den Heever, I ;

Allin, SM ;

Hodkinson, CC ;

Northfield, CJ ;

Page, MI .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (15) :1629-1631

[10] Hepatitis B virus replication is blocked by a 2-hydroxyisoquinoline-1,3(2H,4H)-dione (HID) inhibitor of the viral ribonuclease H activity [J].

Cai, Catherine W. ;

Lomonosova, Elena ;

Moran, Eileen A. ;

Cheng, Xiaohong ;

Patel, Kunjan B. ;

Bailly, Fabrice ;

Cotelle, Philippe ;

Meyers, Marvin J. ;

Tavis, John E. .

ANTIVIRAL RESEARCH, 2014, 108 :48-55

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