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Synthesis 2016; 48(17): 2721-2731
DOI: 10.1055/s-0035-1561672
DOI: 10.1055/s-0035-1561672
short review
Nitrile N-Oxides and Nitrile Imines as New Fuels for the Discovery of Novel Isocyanide-Based Multicomponent Reactions
Further Information
Publication History
Received: 15 April 2016
Accepted after revision: 09 May 2016
Publication Date:
28 June 2016 (online)
Abstract
With this short review we would like to describe our work on isocyanide-mediated multicomponent reactions using the 1,3-dipolar species nitrile N-oxides and nitrile imines as electrophilic inputs. Our goal is to show the potentiality of these transformations, elucidate the mechanisms of the reactions, demonstrate the versatility, and highlight the potentiality of this chemistry.
1 Introduction
2 (Z)-Chloroximes as Electrophilic Partners for Isocyanides
2.1 Precedents for the Reaction Between Nitrile N-Oxides and Isocyanides
2.2 Reaction between (Z)-Chloroximes, Isocyanides, and Carboxylic Acids (or Amines)
2.3 The Use of Other Nucleophiles as the Third Partner
2.4 General Mechanism
3 Nitrile Imines as Electrophilic Partners for Isocyanides
4 Conclusions and Future Outlook
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For other methods to synthesize chloroximes using the reagent N-tert-butyl-N-chlorocyanamide, see:
With the reagent benzyltrimethylammonium tetrachloroiodate, see:
[3+1] Cycloadditions involving an isocyanide have been reported and some four-membered rings were sufficiently stable to undergo X-ray crystal structure analysis. For review articles see: