Literature DB >> 16444296

Azide rearrangements in electron-deficient systems.

S Lang1, J A Murphy.   

Abstract

The azide group has a diverse and extensive role in organic chemistry, reflected in the power of azide anion as a strong nucleophile, the role of organic azides as excellent substrates for cycloaddition reactions, the uses of azides as precursors of amines and nitrenes, and azide rearrangements known as the Curtius and Schmidt reactions. In recent years the scope of the Schmidt reaction has begun to be explored in depth, so that it now represents an important reaction in synthetic chemistry. This tutorial review analyses and summarises key recent developments in the field of Schmidt reactions.

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Year:  2005        PMID: 16444296     DOI: 10.1039/b505080d

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  13 in total

1.  An unexpected copper catalyzed 'reduction' of an arylazide to amine through the formation of a nitrene intermediate.

Authors:  Hanjing Peng; Kednerlin H Dornevil; Alexander B Draganov; Weixuan Chen; Chaofeng Dai; William H Nelson; Aimin Liu; Binghe Wang
Journal:  Tetrahedron       Date:  2013-04-25       Impact factor: 2.457

2.  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

3.  Intramolecular and Intermolecular Schmidt Reactions of Alkyl Azides with Aldehydes.

Authors:  Huey-Lih Lee; Jeffrey Aubé
Journal:  Tetrahedron       Date:  2007-09-03       Impact factor: 2.457

Review 4.  Chemistry of bridged lactams and related heterocycles.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  Chem Rev       Date:  2013-06-17       Impact factor: 60.622

5.  Ethylene in organic synthesis: a new route to anticholenergic pyrrolidinoindolines, and other molecules with all carbon-quaternary centers via asymmetric hydrovinylation.

Authors:  Hwan Jung Lim; T V RajanBabu
Journal:  Org Lett       Date:  2011-11-21       Impact factor: 6.005

6.  Practical Electrochemical Anodic Oxidation of Polycyclic Lactams for Late Stage Functionalization.

Authors:  Kevin J Frankowski; Ruzhang Liu; Gregory L Milligan; Kevin D Moeller; Jeffrey Aubé
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-01       Impact factor: 15.336

7.  Rh2(II)-catalyzed nitro-group migration reactions: selective synthesis of 3-nitroindoles from β-nitro styryl azides.

Authors:  Benjamin J Stokes; Sheng Liu; Tom G Driver
Journal:  J Am Chem Soc       Date:  2011-03-14       Impact factor: 15.419

8.  Stereocontrol in a combined allylic azide rearrangement and intramolecular Schmidt reaction.

Authors:  Ruzhang Liu; Osvaldo Gutierrez; Dean J Tantillo; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2012-04-10       Impact factor: 15.419

9.  Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction.

Authors:  Hashim F Motiwala; Charlie Fehl; Sze-Wan Li; Erin Hirt; Patrick Porubsky; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2013-06-07       Impact factor: 15.419

10.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

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