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Synfacts 2007(9): 0920-0920
DOI: 10.1055/s-2007-968903
DOI: 10.1055/s-2007-968903
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
De Novo Synthesis of 4-Thio- and 4-Aminopyrrole[3,4-c]pyridines
V. S. Berseneva, V. A. Bakulev*, W. Dehaen, S. Toppet, M. Borovkova
The Urals State Technical University, Ekaterinburg, Russian Federation and University of Leuven, Belgium
Further Information
Publication History
Publication Date:
23 August 2007 (online)
Significance
The reported chemistry describes the first efficient synthesis of unprecedented 4-amino- and 4-thio-1,3-dioxo-1H-pyrrole[3,4-c]pyridines, via a one-step reaction between a malonamidine or malonthioamide with methyl acetylpyruvate under mildly basic conditions. In the process, a C-C bond and two new C-N bonds are formed. In addition to its efficiency, broad scope, and use of simple starting materials, facile product isolation of sufficient purity for further chemistry may be noted. The method is anticipated to be suitable for scale-up reactions designed to prepare large amounts of pyrrolo[3,4c]pyridines for biological testing.