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Synthesis 2020; 52(22): 3356-3373
DOI: 10.1055/s-0040-1706402
DOI: 10.1055/s-0040-1706402
feature
One-Pot Synthesis of γ-Azidobutyronitriles and Their Intramolecular Cycloadditions
Research related to the development of a one-pot synthetic approach to azidonitriles was supported by the Russian Science Foundation (19-73-00244). Research related to the development of synthetic procedures for converting azidonitriles into tetrazoles was supported by the Russian Foundation for Basic Research (18-53-41009), and by the Ministry of Innovative Development of the Republic of Uzbekistan (MRU-FA-74/2017).Further Information
Publication History
Received: 19 May 2020
Accepted after revision: 22 June 2020
Publication Date:
04 August 2020 (online)
Abstract
Efficient gram-scale, one-pot approaches to azidocyanobutyrates and their amidated or decarboxylated derivatives have been developed, starting from commercially available aldehydes and cyanoacetates. These techniques combine (1) Knoevenagel condensation, (2) Corey–Chaykovsky cyclopropanation and (3) nucleophilic ring opening of donor-acceptor cyclopropanes with the azide ion, as well as (4) Krapcho decarboxylation or (4′) amidation. The synthetic utility of the resulting γ-azidonitriles was demonstrated by their transformation into tetrazoles via intramolecular (3+2)-cycloaddition. A condition-dependent activation effect of the α-substituent was revealed in that case. Thermally activated azide–nitrile interaction did not differentiate the presence of an α-electron-withdrawing substituent in γ-azidonitriles, whereas the Lewis acid mediated (SnCl4 or TiCl4) reaction proceeded much easier for azidocyanobutyrates. This allowed us to develop an efficient procedure for converting azidocyanobutyrates into the corresponding tetrazoles.
Key words
azides - nitriles - one-pot synthesis - 1,3-dipolar cycloaddition - tetrazoles - Knoevenagel condensation - Corey–Chaykovsky reaction - nucleophilic ring openingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706402.
- Supporting Information
- CIF File
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