Synthesis 2014; 46(11): 1463-1468
DOI: 10.1055/s-0033-1341101
paper
© Georg Thieme Verlag Stuttgart · New York

Facile Direct Synthesis of Acetylenedicarboxamides

Dirk Heyl
Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Alarich-Weiss-Straße 4, 64287 Darmstadt, Germany   Fax: +49(6151)166636   Email: fessner@tu-darmstadt.de
,
Wolf-Dieter Fessner*
Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Alarich-Weiss-Straße 4, 64287 Darmstadt, Germany   Fax: +49(6151)166636   Email: fessner@tu-darmstadt.de
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Publication History

Received: 13 January 2014

Accepted after revision: 11 February 2014

Publication Date:
17 March 2014 (online)


Abstract

A convenient, rapid and widely applicable one-pot procedure has been developed for the synthesis of acetylenedicarboxamides from various primary and secondary amines, including amino acid derivatives, protected carbohydrates, and fluorescent labels. By using DMTMM for amide coupling, acetylenedicarboxylic acid was directly converted into acetylenedicarboxamides in highly competitive overall yields (52–80%).

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