Publication: Unexpected reaction course of 3-Amino-5-aryl-1H-pyrazoles with Dialkyl Dicyanofumarates
Unexpected reaction course of 3-Amino-5-aryl-1H-pyrazoles with Dialkyl Dicyanofumarates
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Ali, K. A., Ragab, E. A., Mlostoń, G., Celeda, M., Linden, A., & Heimgartner, H. (2013). Unexpected reaction course of 3-Amino-5-aryl-1H-pyrazoles with Dialkyl Dicyanofumarates. Helvetica Chimica Acta, 96(4), 633–643. https://doi.org/10.1002/hlca.201200633
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On treatment of 3-amino-5-aryl-1H-pyrazoles 1 with dialkyl dicyanofumarates (=(E)-but-2-enedioates) 4 in boiling 1,2-dichloroethane, two competitive reactions occurred leading to 3-aryl-5-cyano-6,7-dihydro-6-oxo-1H-pyrazolo[3,4-b]pyridine-4-carboxylates 10 and 7-amino-2-arylpyrazolo[1,5-a]pyrimidine-5,6-dicarboxylates 11. In DMF at room temperature, as well as at 100°, only compounds 10 were isolated. The formation of the major products of type 10 was rationalized via Michael addition of 1 as a C(4)-nucleophile onto 4, followed by HCN
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- Ali, Korany A
- Ragab, Eman A
- Mlostoń, Grzegorz
- Celeda, Malgorzata
- Heimgartner, Heinz
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Ali, K. A., Ragab, E. A., Mlostoń, G., Celeda, M., Linden, A., & Heimgartner, H. (2013). Unexpected reaction course of 3-Amino-5-aryl-1H-pyrazoles with Dialkyl Dicyanofumarates. Helvetica Chimica Acta, 96(4), 633–643. https://doi.org/10.1002/hlca.201200633
