Literature DB >> 25029554

Facile access to functionalized spiro[indoline-3,2'-pyrrole]-2,5'-diones via post-Ugi domino Buchwald-Hartwig/Michael reaction.

Nandini Sharma1, Zhenghua Li, Upendra K Sharma, Erik V Van der Eycken.   

Abstract

A novel access to spiro[indoline-3,2'-pyrrole]-2,5'-diones is presented via a palladium-catalyzed post-Ugi cascade cyclization approach involving a Buchwald-Hartwig/Michael reaction sequence. The method allows the easy construction of a library of spirooxindoles in moderate to good yields starting from readily available precursors. In addition, alkynoic acids are replaced with α,β-unsaturated acids leading to variably substituted spirooxindoles.

Entities:  

Year:  2014        PMID: 25029554     DOI: 10.1021/ol5019079

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  9 in total

Review 1.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

2.  Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds.

Authors:  Shima Dianat; Mohammad Mahdavi; Setareh Moghimi; Arash Mouradzadegun; Abbas Shafiee; Alireza Foroumadi
Journal:  Mol Divers       Date:  2015-08-01       Impact factor: 2.943

3.  Catalyst free, C-3 functionalization of imidazo[1,2-a]pyridines to rapidly access new chemical space for drug discovery efforts.

Authors:  Naresh Gunaganti; Anupreet Kharbanda; Naga Rajiv Lakkaniga; Lingtian Zhang; Rose Cooper; Hong-Yu Li; Brendan Frett
Journal:  Chem Commun (Camb)       Date:  2018-11-15       Impact factor: 6.222

Review 4.  Recent advances in the development of polycyclic skeletons via Ugi reaction cascades.

Authors:  Jie Lei; Jiang-Ping Meng; Dian-Yong Tang; Brendan Frett; Zhong-Zhu Chen; Zhi-Gang Xu
Journal:  Mol Divers       Date:  2018-01-16       Impact factor: 2.943

5.  Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael-Henry cascade reactions.

Authors:  Yonglei Du; Jian Li; Kerong Chen; Chenglin Wu; Yu Zhou; Hong Liu
Journal:  Beilstein J Org Chem       Date:  2017-07-07       Impact factor: 2.883

Review 6.  Post-Ugi Cyclization for the Construction of Diverse Heterocyclic Compounds: Recent Updates.

Authors:  Jitender Bariwal; Rupinder Kaur; Leonid G Voskressensky; Erik V Van der Eycken
Journal:  Front Chem       Date:  2018-11-20       Impact factor: 5.221

7.  Facile synthesis and biological evaluation of tryptamine-piperazine-2,5-dione conjugates as anticancer agents.

Authors:  Jiang-Ping Meng; Shi-Qiang Li; Yan Tang; Zhi-Gang Xu; Zhong-Zhu Chen; Li-Xia Gao
Journal:  RSC Adv       Date:  2021-08-17       Impact factor: 4.036

8.  Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3-Isothiocyanato Oxindoles with Dibenzylidene Ketones.

Authors:  Dan Du; Yu Jiang; Qin Xu; Xiao-Ge Li; Min Shi
Journal:  ChemistryOpen       Date:  2016-05-25       Impact factor: 2.911

9.  Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence.

Authors:  Amarendar Reddy Maddirala; Peter R Andreana
Journal:  Beilstein J Org Chem       Date:  2018-04-18       Impact factor: 2.883

  9 in total

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