Literature DB >> 16953613

Versatile, fragrant, convertible isonitriles.

Michael C Pirrung1, Subir Ghorai.   

Abstract

The metalation of oxazoles leads to ring opening to the isocyanoenolate that can be O-acylated to give the unsaturated isonitriles. These substances undergo conventional multicomponent reactions. The products of their reactions are readily converted to acyl substitution products by treatment with acid and a nucleophile. These unsaturated isonitriles are notable by their simple preparations and, unusually, their nonoffensive odors.

Entities:  

Year:  2006        PMID: 16953613     DOI: 10.1021/ja0644374

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


  6 in total

1.  Studies on the chemistry and reactivity of alpha-substituted ketones in isonitrile-based multicomponent reactions.

Authors:  Lijun Fan; Ashley M Adams; Jason G Polisar; Bruce Ganem
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

2.  Applications of the Ugi reaction with ketones.

Authors:  Suvi T M Simila; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2008       Impact factor: 2.415

3.  Structure-Activity and Structure-Toxicity Relationships of Peptoid-Based Histone Deacetylase Inhibitors with Dual-Stage Antiplasmodial Activity.

Authors:  Marcel K W Mackwitz; Eva Hesping; Yevgeniya Antonova-Koch; Daniela Diedrich; Tamirat Gebru Woldearegai; Tina Skinner-Adams; Mary Clarke; Andrea Schöler; Laura Limbach; Thomas Kurz; Elizabeth A Winzeler; Jana Held; Katherine T Andrews; Finn K Hansen
Journal:  ChemMedChem       Date:  2019-02-19       Impact factor: 3.466

Review 4.  Emerging molecular diversity from the intra-molecular Ugi reaction: iterative efficiency in medicinal chemistry.

Authors:  Christopher Hulme; Justin Dietrich
Journal:  Mol Divers       Date:  2009-02-11       Impact factor: 3.364

5.  Tuning π-Acceptor/σ-Donor Ratio of the 2-Isocyanoazulene Ligand: Non-Fluorinated Rival of Pentafluorophenyl Isocyanide and Trifluorovinyl Isocyanide Discovered.

Authors:  Mason D Hart; John J Meyers; Zachary A Wood; Toshinori Nakakita; Jason C Applegate; Nathan R Erickson; Nikolay N Gerasimchuk; Mikhail V Barybin
Journal:  Molecules       Date:  2021-02-12       Impact factor: 4.411

Review 6.  Isocyanide-Based Multicomponent Reactions for the Synthesis of Heterocycles.

Authors:  András Váradi; Travis C Palmer; Rebecca Notis Dardashti; Susruta Majumdar
Journal:  Molecules       Date:  2015-12-23       Impact factor: 4.411

  6 in total

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