Literature DB >> 24791030

Mild oxidation of tosylmethylisocyanide to tosylmethylisocyanate: utility in synthetic and medicinal chemistry.

Hoang V Le1, Bruce Ganem1.   

Abstract

A convenient and efficient (one-step) oxidation is reported of commercially available tosylmethylisocyanide (TOSMIC) to form tosylmethylisocyanate, making this highly reactive bifunctional molecule a readily available synthetic reagent. Besides engaging in nucleophilic addition reactions with alcohols, amines and thiols, tosylmethylisocyanate also reacts with carboxylic acids to form tosylmethylamides, which undergo substitution reactions in the presence of organocopper and organomagnesium reagents.

Entities:  

Keywords:  Isonitrile-based Multicomponent reactions; Tosylmethylamide; Tosylmethylisocyanate; Tosylmethylisocyanide; p-Toluenesulfonylmethyl isocyanate

Year:  2014        PMID: 24791030      PMCID: PMC4001987          DOI: 10.1016/j.tetlet.2014.02.016

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  2 in total

1.  Trifluoroacetic anhydride-catalyzed oxidation of isonitriles by DMSO: a rapid, convenient synthesis of isocyanates.

Authors:  Hoang V Le; Bruce Ganem
Journal:  Org Lett       Date:  2011-04-14       Impact factor: 6.005

2.  Facile amide bond formation from carboxylic acids and isocyanates.

Authors:  Kaname Sasaki; David Crich
Journal:  Org Lett       Date:  2011-03-23       Impact factor: 6.005

  2 in total
  1 in total

Review 1.  The status of isocyanide-based multi-component reactions in Iran (2010-2018).

Authors:  Ronak Afshari; Seyyed Emad Hooshmand; Mohammad Taghi Nazeri; Siamak Javanbakht; Ahmad Shaabani; Reza Mohammadian
Journal:  Mol Divers       Date:  2020-02-18       Impact factor: 2.943

  1 in total

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