Literature DB >> 14682773

Radical cyclization cascade involving ynamides: an original access to nitrogen-containing heterocycles.

Frédéric Marion1, Christine Courillon, Max Malacria.   

Abstract

A radical cascade involving a 5-exo-dig cyclization followed by a 6-endo-trig radical trapping transforms ynamides into heterogeneous polycyclic compounds in good yields. This leads interestingly to the formation of isoindols, isoindolinones, and pyridoisoindolones. [reaction: see text]

Entities:  

Year:  2003        PMID: 14682773     DOI: 10.1021/ol036177q

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


  4 in total

Review 1.  Ynamides: a modern functional group for the new millennium.

Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

2.  The Domino Way to Heterocycles.

Authors:  Albert Padwa; Scott K Bur
Journal:  Tetrahedron       Date:  2007-06-18       Impact factor: 2.457

3.  Stereoselective additions of thiyl radicals to terminal ynamides.

Authors:  Biplab Banerjee; Dmitry N Litvinov; Junghoon Kang; Jennifer D Bettale; Steven L Castle
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

4.  SYNTHESIS OF YNAMIDES BY N-ALKYNYLATION OF AMINE DERIVATIVES. PREPARATION OF N-ALLYL-N-(METHOXYCARBONYL)-1,3-DECADIYNYLAMINE.

Authors:  Amanda L Kohnen; Joshua R Dunetz; Rick L Danheiser
Journal:  Organic Synth       Date:  2007
  4 in total

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