Application of Isocyanides as Amide Surrogates in the Synthesis of Diverse Isoindolin-1-one Derivatives by a Palladium-Catalyzed Tandem Carboxamidation/Hydroamidation Reaction

被引：29

作者：

Pathare, Ramdas S. ^{[1
]}

Sharma, Shivani ^{[1
]}

Elagandhula, Sathish ^{[2
]}

Saini, Vaishali ^{[2
]}

Sawant, Devesh M. ^{[2
]}

Yadav, Monika ^{[3
]}

Sharon, Ashoke ^{[3
]}

Khan, Shahnawaz ^{[4
]}

Pardasani, Ram T. ^{[1
]}

机构：

[1] Cent Univ Rajasthan, SCSP, Dept Chem, Kishangarh 305817, Rajasthan, India

[2] Cent Univ Rajasthan, SCSP, Dept Pharm, Kishangarh 305817, Rajasthan, India

[3] Birla Inst Technol, Dept Chem, Ranchi 835215, Jharkhand, India

[4] Univ Rajasthan, Dept Chem, JLN Marg, Jaipur 302004, Rajasthan, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 33期

关键词：

Cyclization; Insertion; Nitrogen heterocycles; Regioselectivity; Domino reactions; SUBSTITUTED; 3-METHYLENEISOINDOLIN-1-ONES; MULTICOMPONENT REACTIONS; ASYMMETRIC-SYNTHESIS; EFFICIENT; ACCESS; HETEROCYCLES; CYCLIZATION; INSERTION; CARBONYLATION; AMINATION;

D O I：

10.1002/ejoc.201600999

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rapid synthesis of the isoindolinone skeleton has been accomplished by a palladium-catalyzed one-pot tandem process, which consists of an isocyanide insertion/hydration (carboxamidation) and 5-exo-dig cycloisomerization (hydroamidation) reaction sequence that afforded the products in good to excellent yields. Preliminary mechanistic studies of this sequential C-C/C-O/C-N bond formation process suggests that the carboxamidation step is palladium-dependent, whereas the hydroamidation step is solely mediated by the base and is driven by the electrophilicity of the alkyne.

引用

页码：5579 / 5587

页数：9

共 82 条

[1] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[2] Kinetic Data on the Synergetic Role of Amines and Water in the Reduction of Phosphine-Ligated Palladium(II) to Palladium(0) [J].

Amatore, Christian ;

El Kaim, Laurent ;

Grimaud, Laurence ;

Jutand, Anny ;

Meignie, Alice ;

Romanov, Georgy .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (22) :4709-4713

[3]

[Anonymous], 2008, ANGEW CHEM

[4]

[Anonymous], 2013, ANGEW CHEM

[5]

[Anonymous], 1991, J.P.H. Patent, Patent No. [03,133,955, 03133955]

[6] Solvent-free Multicomponent Synthesis of Biologically-active Fused-imidazo Heterocycles Catalyzed by Reusable Yb(OTf)3 Under Microwave Irradiation [J].

Ansari, Arshad J. ;

Sharma, Shivani ;

Pathare, Ramdas S. ;

Gopal, Kandasamy ;

Sawant, Devesh M. ;

Pardasani, R. T. .

CHEMISTRYSELECT, 2016, 1 (05) :1016-1021

[7] 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

[8] Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium-Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates [J].

Barrio, Pablo ;

Ibanez, Ignacio ;

Herrera, Lidia ;

Roman, Raquel ;

Catalan, Silvia ;

Fustero, Santos .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (32) :11579-11584

[9] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].

Beller, M ;

Seayad, J ;

Tillack, A ;

Jiao, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398

[10]

Beller M, 2004, ANGEW CHEM, V116, P3448

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