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Synthesis 2018; 50(09): 1891-1900
DOI: 10.1055/s-0036-1591905
DOI: 10.1055/s-0036-1591905
paper
Expeditious Scalable Catalyst-Free One-Pot Synthesis of 4-Alkoxy-5-amino-3-methylthiophene-2-carbonitriles via Sequential Reactions of Lithiated Alkoxyallenes with Isothiocyanates and 2-Bromoacetonitrile
This work was made possible through financial support from the Russian Foundation for Basic Research (Grant No. 16-03-00234a).Further Information
Publication History
Received: 22 November 2017
Accepted after revision: 26 December 2017
Publication Date:
29 January 2018 (online)
Abstract
A synthetically simple and convenient approach to tetrasubstituted thiophenes with rare combination of the alkoxy, amino, and cyano groups has been developed. The assembly of polyfunctionalized thiophene ring is implemented in one preparative step by sequential addition of isothiocyanate and 2-bromoacetonitrile to the lithiated (with n-BuLi) alkoxyallene. The reaction proceeds through in situ formation and intramolecular cyclization of cyanomethyl 2-alkoxy-N-buta-2,3-dienimidothioate (1-aza-1,3,4-triene).
Key words
alkoxyallenes - isothiocyanates - 2-bromoacetonitrile - 1-aza-1,3,4-trienes - 4-alkoxy-5-amino-3-methylthiophene-2-carbonitrilesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591905.
- Supporting Information
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