Literature DB >> 28737400

Synthesis of Spirooxindoles via the tert-Amino Effect.

Kinthada Ramakumar1,2, Tapan Maji1,2, James J Partridge1,2, Jon A Tunge1,2.   

Abstract

A new method is developed for the synthesis of spirooxindoles from amines and isatins via C-H functionalization. The reaction leverages the tert-amino effect to form an enolate-iminium intermediate via [1,5]-hydride shift followed by cyclization. Interestingly the hydride migrates to the N atom of a C═N, which is atypical for hydride additions to imines.

Entities:  

Mesh:

Substances:

Year:  2017        PMID: 28737400     DOI: 10.1021/acs.orglett.7b01752

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


  6 in total

1.  Redox-Annulations of Cyclic Amines with ortho-Cyanomethylbenzaldehydes.

Authors:  Anirudra Paul; Hemant S Chandak; Longle Ma; Daniel Seidel
Journal:  Org Lett       Date:  2020-01-27       Impact factor: 6.005

2.  α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines.

Authors:  Anirudra Paul; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2019-05-24       Impact factor: 15.419

3.  Redox-Annulations of Cyclic Amines with Electron-Deficient o-Tolualdehydes.

Authors:  Anirudra Paul; Alafate Adili; Daniel Seidel
Journal:  Org Lett       Date:  2019-03-06       Impact factor: 6.005

4.  Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.

Authors:  Zhengbo Zhu; Hemant S Chandak; Daniel Seidel
Journal:  Org Lett       Date:  2018-06-25       Impact factor: 6.005

Review 5.  Transition metal-catalyzed synthesis of spirooxindoles.

Authors:  P V Saranya; Mohan Neetha; Thaipparambil Aneeja; Gopinathan Anilkumar
Journal:  RSC Adv       Date:  2021-02-10       Impact factor: 3.361

Review 6.  The Cascade [1,5]-Hydride Shift/Intramolecular C(sp3)-H Activation: A Powerful Approach to the Construction of Spiro-Tetrahydroquinoline Skeleton.

Authors:  Hongmei Liu; Yunyun Quan; Long Xie; Xiang Li; Xin Xie
Journal:  Front Chem       Date:  2022-04-07       Impact factor: 5.545

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.