Literature DB >> 35925529

1,3-Dipolar cycloaddition reactions of isatin-derived azomethine ylides for the synthesis of spirooxindole and indole-derived scaffolds: recent developments.

Fatemeh Rostami Miankooshki1, Mohammad Bayat2, Shima Nasri1, Narges Habibi Samet1.   

Abstract

The unique therapeutic and biological characteristics of spirooxindole have led to the presentation of numerous reactions for the synthesis of spirooxindoles through 1,3-Dipolar cycloaddition of highly reactive isatin-derived azomethine ylides with activated olefins as the main tool for the formation of spirocyclic oxindoles during the last 4 years. Therefore, there is a need to highlight the recent developments in this area, along with the representative synthetic methods and relevant reaction mechanisms from 2018 to 2021. The representative synthetic methodologies were listed in four sections based on the procedure to form the azomethine ylide species including isatins and amino acids, isatin-derived α-(trifluoromethyl)imine, isatins and benzylamines, and from isatin-derived cyclic imine 1,3-dipoles.
© 2022. The Author(s), under exclusive licence to Springer Nature Switzerland AG.

Entities:  

Keywords:  1,3-Dipolar cycloaddition; Azomethine ylide; Dipolarophile; Isatin; Spirooxindole; Spirooxindole pyrrolidine

Year:  2022        PMID: 35925529     DOI: 10.1007/s11030-022-10510-9

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   3.364


  49 in total

1.  The decarboxylative Strecker reaction.

Authors:  Deepankar Das; Matthew T Richers; Longle Ma; Daniel Seidel
Journal:  Org Lett       Date:  2011-11-16       Impact factor: 6.005

2.  Transition-Metal-Free Access to Pyridocarbazoles from 2-Alkynylindole-3-carbaldehydes via Azomethine Ylide.

Authors:  Shalini Verma; Pawan K Mishra; Manoj Kumar; Souvik Sur; Akhilesh K Verma
Journal:  J Org Chem       Date:  2018-06-06       Impact factor: 4.354

3.  Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids.

Authors:  Evgeny M Buev; Vladimir S Moshkin; Vyacheslav Y Sosnovskikh
Journal:  J Org Chem       Date:  2017-11-01       Impact factor: 4.354

4.  Recent advances in spirocyclization of indole derivatives.

Authors:  Jitender Bariwal; Leonid G Voskressensky; Erik V Van der Eycken
Journal:  Chem Soc Rev       Date:  2018-06-05       Impact factor: 54.564

5.  Synthesis of Spiro[oxindole-3,2'-pyrrolidine] Derivatives from Benzynes and Azomethine Ylides through 1,3-Dipolar Cycloaddition Reactions.

Authors:  Heesun Ryu; Jeongseob Seo; Haye Min Ko
Journal:  J Org Chem       Date:  2018-10-30       Impact factor: 4.354

Review 6.  Novel Hybrid Molecules Based on triazole-β-lactam as Potential Biological Agents.

Authors:  Pezhman Shiri
Journal:  Mini Rev Med Chem       Date:  2021       Impact factor: 3.862

7.  Asymmetric [3 + 2] Cycloaddition Reaction of Isatin-Derived MBH Carbonates with 3-Methyleneoxindoles: Enantioselective Synthesis of 3,3'-Cyclopentenyldispirooxindoles Incorporating Two Adjacent Quaternary Spirostereocenters.

Authors:  Yu Chen; Bao-Dong Cui; Yi Wang; Wen-Yong Han; Nan-Wei Wan; Mei Bai; Wei-Cheng Yuan; Yong-Zheng Chen
Journal:  J Org Chem       Date:  2018-07-11       Impact factor: 4.354

Review 8.  The azomethine ylide route to amine C-H functionalization: redox-versions of classic reactions and a pathway to new transformations.

Authors:  Daniel Seidel
Journal:  Acc Chem Res       Date:  2015-01-06       Impact factor: 22.384

Review 9.  A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles.

Authors:  Pezhman Shiri; Ali Mohammad Amani; Thomas Mayer-Gall
Journal:  Beilstein J Org Chem       Date:  2021-07-13       Impact factor: 2.883

Review 10.  Recent Applications of Diversity-Oriented Synthesis Toward Novel, 3-Dimensional Fragment Collections.

Authors:  Sarah L Kidd; Thomas J Osberger; Natalia Mateu; Hannah F Sore; David R Spring
Journal:  Front Chem       Date:  2018-10-16       Impact factor: 5.221

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