Literature DB >> 16144378

Interrupted Nazarov cyclization on silica gel.

Francis Dhoro1, Marcus A Tius.   

Abstract

Exposure of a mixture of propargyl vinyl ketone and a nucleophilic primary or secondary amine to activated dry silica gel in the absence of solvent leads to a cascade of reactions that results in the formation of an aminocyclopentenone. The reaction with triethylamine leads to a cross-conjugated cyclopentadienone.

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Year:  2005        PMID: 16144378     DOI: 10.1021/ja053393g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  9 in total

1.  Intramolecular azide trapping of the Nazarov intermediate: formation of peroxy-bridged indolizidinones via a deep-seated rearrangement and aerobic oxidation.

Authors:  Ali Rostami; Yong Wang; Atta M Arif; Robert McDonald; F G West
Journal:  Org Lett       Date:  2007-01-26       Impact factor: 6.005

2.  Asymmetric amine-intercepted Nazarov cyclization.

Authors:  Francis Dhoro; Tor E Kristensen; Vegar Stockmann; Glenn P A Yap; Marcus A Tius
Journal:  J Am Chem Soc       Date:  2007-05-18       Impact factor: 15.419

3.  Understanding the fate of the oxyallyl cation following Nazarov electrocyclization: sequential Wagner-Meerwein migrations and the synthesis of spirocyclic cyclopentenones.

Authors:  Jie Huang; David Lebœuf; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2011-04-05       Impact factor: 15.419

4.  α-Aryl-substituted allenamides in an imino-Nazarov cyclization cascade catalyzed by Au(I).

Authors:  Zhi-Xiong Ma; Shuzhong He; Wangze Song; Richard P Hsung
Journal:  Org Lett       Date:  2012-11-02       Impact factor: 6.005

5.  Beyond the Divinyl Ketone: Innovations in the Generation and Nazarov Cyclization of Pentadienyl Cation Intermediates.

Authors:  William T Spencer; Tulaza Vaidya; Alison J Frontier
Journal:  European J Org Chem       Date:  2013-06-01

6.  Interrupting the Nazarov cyclization with indoles.

Authors:  Ashok K Basak; Marcus A Tius
Journal:  Org Lett       Date:  2008-08-23       Impact factor: 6.005

7.  Cooperative benzylic-oxyallylic stabilized cations: regioselective construction of α-quaternary centers in ketone-derived compounds.

Authors:  Nitin S Dange; Jacob R Stepherson; Caitlan E Ayala; Frank R Fronczek; Rendy Kartika
Journal:  Chem Sci       Date:  2015-07-22       Impact factor: 9.825

8.  The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues.

Authors:  Ronny William; Wei Lin Leng; Siming Wang; Xue-Wei Liu
Journal:  Chem Sci       Date:  2015-10-27       Impact factor: 9.825

9.  Novel d-Annulated Pentacyclic Steroids: Regioselective Synthesis and Biological Evaluation in Breast Cancer Cells.

Authors:  Svetlana K Vorontsova; Anton V Yadykov; Alexander M Scherbakov; Mikhail E Minyaev; Igor V Zavarzin; Ekaterina I Mikhaevich; Yulia A Volkova; Valerii Z Shirinian
Journal:  Molecules       Date:  2020-07-31       Impact factor: 4.411

  9 in total

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