Literature DB >> 28439765

FeCl₃-catalyzed [3+3] annulation between 3-oxirane-indolin-2-ones and nitrones to construct spiro[1,4,2-dioxazinan]oxindoles.

Jingmiao Yu1, Chun Cai2.   

Abstract

An efficient and mild procedure for the synthesis of spiro[1,4,2-dioxazinan]oxindoles has been achieved in high yields by [Formula: see text]-catalyzed annulation of 3-oxirane-indolin-2-ones and nitrones. This catalytic protocol demonstrates that the reaction could tolerate a variety of functional groups and provides convenient access to new structural motifs in good to excellent yields. Moreover, this method featured relatively short reaction time and easy operation.

Entities:  

Keywords:  Annulation; Nitrone; Ring expansion; Spirooxindole

Mesh:

Substances:

Year:  2017        PMID: 28439765     DOI: 10.1007/s11030-017-9741-z

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  36 in total

1.  Tungsten-promoted [3 + 2]- and [3 + 3]-cycloaddition of epoxides with alkynes. A facile enantiospecific synthesis of bicyclic lactones.

Authors:  R J Madhushaw; C L Li; K H Shen; C C Hu; R S Liu
Journal:  J Am Chem Soc       Date:  2001-08-01       Impact factor: 15.419

2.  Lewis acid catalyzed asymmetric cycloadditions of nitrones: alpha'-hydroxy enones as efficient reaction partners.

Authors:  Claudio Palomo; Mikel Oiarbide; Elena Arceo; Jesús M García; Rosa López; Alberto González; Anthony Linden
Journal:  Angew Chem Int Ed Engl       Date:  2005-09-26       Impact factor: 15.336

3.  Highly enantioselective and diastereoselective cycloaddition of cyclopropanes with nitrones and its application in the kinetic resolution of 2-substituted cyclopropane-1,1-dicarboxylates.

Authors:  Yan-Biao Kang; Xiu-Li Sun; Yong Tang
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles and epoxides: regioselective synthesis of substituted 3,4-dihydro-2H-1,4-oxazines.

Authors:  Xueji Ma; Shanfei Pan; Hangxiang Wang; Wanzhi Chen
Journal:  Org Lett       Date:  2014-08-21       Impact factor: 6.005

5.  Cobalt-catalyzed cyclization of carbon monoxide, imine, and epoxide.

Authors:  Yubo Zhang; Jiamin Ji; Xiuliang Zhang; Shaohui Lin; Qinmin Pan; Li Jia
Journal:  Org Lett       Date:  2014-03-28       Impact factor: 6.005

6.  Studies on the formal [3 + 2] cycloaddition of aziridines with alkenes for the synthesis of 1-azaspiroalkanes.

Authors:  Elodie Martinand-Lurin; Raymond Gruber; Pascal Retailleau; Paul Fleurat-Lessard; Philippe Dauban
Journal:  J Org Chem       Date:  2015-01-12       Impact factor: 4.354

7.  Enantioselective synthesis of 4,5-dihydropyrroles via domino ring-opening cyclization (DROC) of N-activated aziridines with malononitrile.

Authors:  Manas K Ghorai; Deo Prakash Tiwari
Journal:  J Org Chem       Date:  2013-02-19       Impact factor: 4.354

8.  Lewis Acid Catalyzed Annulation of Nitrones with Oxiranes, Aziridines, and Thiiranes.

Authors:  Stalin R Pathipati; Vipender Singh; Lars Eriksson; Nicklas Selander
Journal:  Org Lett       Date:  2015-09-02       Impact factor: 6.005

Review 9.  Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

Authors:  Chris V Galliford; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

10.  Lewis acid-promoted carbon-carbon bond cleavage of aziridines: divergent cycloaddition pathways of the derived ylides.

Authors:  Patrick D Pohlhaus; Roy K Bowman; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2004-03-03       Impact factor: 15.419

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