Literature DB >> 36157552

Three-Component [3+2] Cycloaddition for Regio- and Diastereoselective Synthesis of Spirooxindole-Pyrrolidines.

Xiaofeng Zhang1,2, Miao Liu1, Desheng Zhan3, Manpreet Kaur4, Jerry P Jasinski4, Wei Zhang1.   

Abstract

1,3-Dipolar cycloaddition of nonstabilized azomethine ylides derived from α-C-H functionalization of tetrahydroisoquinoline for regio- and diastereoselective synthesis of spirooxindole-pyrrolidines is developed. A three-component reaction of readily available cyclic amine, aryl aldehydes, and olefinic oxindoles provides a pot, atom and step economy (PASE) approach for making spiro-heterocyclic compounds with biological interest.

Entities:  

Year:  2022        PMID： 36157552      PMCID： PMC9496578          DOI： 10.1039/d1nj05538k

Source DB:  PubMed          Journal:  New J Chem        ISSN： 1144-0546            Impact factor:   3.925


  46 in total

1.  Organocatalytic synthesis of spiro[pyrrolidin-3,3'-oxindoles] with high enantiopurity and structural diversity.

Authors:  Xiao-Hua Chen; Qiang Wei; Shi-Wei Luo; Han Xiao; Liu-Zhu Gong
Journal:  J Am Chem Soc       Date:  2009-09-30       Impact factor: 15.419

Review 2.  Catalytic asymmetric construction of spiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides.

Authors:  Xin Fang; Chun-Jiang Wang
Journal:  Org Biomol Chem       Date:  2018-04-18       Impact factor: 3.876

3.  One-Pot Double [3 + 2] Cycloadditions for Diastereoselective Synthesis of Pyrrolidine-Based Polycyclic Systems.

Authors:  Xiaofeng Zhang; Weiqi Qiu; Xiaoming Ma; Jason Evans; Manpreet Kaur; Jerry P Jasinski; Wei Zhang
Journal:  J Org Chem       Date:  2018-10-18       Impact factor: 4.354

Review 4.  Strategies for the enantioselective synthesis of spirooxindoles.

Authors:  Nicolas R Ball-Jones; Joseph J Badillo; Annaliese K Franz
Journal:  Org Biomol Chem       Date:  2012-05-14       Impact factor: 3.876

5.  2-Azaallyl Anions, 2-Azaallyl Cations, 2-Azaallyl Radicals, and Azomethine Ylides.

Authors:  Shaojian Tang; Xia Zhang; Jiayue Sun; Dawen Niu; Jason J Chruma
Journal:  Chem Rev       Date:  2018-10-10       Impact factor: 60.622

6.  Pot economy and one-pot synthesis.

Authors:  Yujiro Hayashi
Journal:  Chem Sci       Date:  2016-01-06       Impact factor: 9.825

7.  One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions.

Authors:  Xiaoming Ma; Xiaofeng Zhang; Weiqi Qiu; Wensheng Zhang; Bruce Wan; Jason Evans; Wei Zhang
Journal:  Molecules       Date:  2019-02-08       Impact factor: 4.411

8.  Three-Component Access to Functionalized Spiropyrrolidine Heterocyclic Scaffolds and Their Cholinesterase Inhibitory Activity.

Authors:  Sarra Boudriga; Saoussen Haddad; Vikneswaran Murugaiyah; Moheddine Askri; Michael Knorr; Carsten Strohmann; Christopher Golz
Journal:  Molecules       Date:  2020-04-23       Impact factor: 4.411

9.  Synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines via three-component [3 + 2] cycloaddition followed by one-pot N-allylation and intramolecular Heck reactions.

Authors:  Xiaoming Ma; Suzhi Meng; Xiaofeng Zhang; Qiang Zhang; Shenghu Yan; Yue Zhang; Wei Zhang
Journal:  Beilstein J Org Chem       Date:  2020-06-04       Impact factor: 2.883

Review 10.  Recent Small-Molecule Inhibitors of the p53-MDM2 Protein-Protein Interaction.

Authors:  Anastasia Beloglazkina; Nikolai Zyk; Alexander Majouga; Elena Beloglazkina
Journal:  Molecules       Date:  2020-03-07       Impact factor: 4.411
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