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Synfacts 2011(7): 0717-0717  
DOI: 10.1055/s-0030-1260516
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 3-Aminocoumarin and Derivatives via Copper Catalysis

Contributor(s): Victor Snieckus, Toni Rantanen
T. Meng, Y. Zou, O. Khorev, Y. Jin, H. Zhou, Y. Zhang, D. Hu, L. Ma, X. Wang, J. Shen*
Shanghai Institute of Materia Medica, P. R. of China and University of Bern, Switzerland
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

Reported is a synthesis of 3-amino-coumarins (A), 3-methylideneaminocoumarins (B), and chromeno[3,4-d]imidazol-4(1H)ones (C) by reaction of ortho-hydroxy acetophenones and salicylaldehydes with isocyanoacetate and amines. This investigation was prompted by the isolation and characterization of a major byproduct from an attempted synthesis of 3-aminoimidazopyridines, which turned out to be a 3-formamidocoumarin A. The yields in the syntheses are generally moderate to good and the substrate scope was reasonably well studied. The conditions given are optimized; other copper sources or bases afforded drastically reduced yields. No data on optimization of the copper amount was provided.