Synthesis of 4-trifluoromethyl pyridazines via annulation of pyridinium ylides with trifluoroacetyl diazoester.

A base promoted annulation of pyridinium ylides with trifluoroacetyl diazoester has been reported. Highly functionalized 4-trifluoromethyl pyridazines were synthesized in good yields without the use of any heavy metal catalysts. The developed methodology was compatible with a variety of important functional groups. Mechanistic studies revealed that trifluoroacetylated hydrazone was an active intermediate of this three-component annulation. Synthetic versatility of the method via aminolysis and condensation toward amide- and pyridazino[4,5-c]pyridazine-derivatives has been showcased.

Citation

Zheng Fang, Yun Teng, Huilin Yang, Rongxing Li, Qiuhong Li, Yi You, Zhiqiang Weng. Synthesis of 4-trifluoromethyl pyridazines via annulation of pyridinium ylides with trifluoroacetyl diazoester. Organic & biomolecular chemistry. 2022 May 04;20(17):3564-3569

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PMID: 35420110

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