Synthesis of 4-trifluoromethyl pyridazines via annulation of pyridinium ylides with trifluoroacetyl diazoester. Issue 17 (14th April 2022)

• Record Type: Journal Article
• Authors: Fang, Zheng; Teng, Yun; Yang, Huilin; Li, Rongxing; Li, Qiuhong; You, Yi; Weng, Zhiqiang
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 17(2022)
• Page Start: 3564
• Page End: 3569
• Publication Date: 2022-04-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00483f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A base promoted annulation of pyridinium ylides with trifluoroacetyl diazoester for the synthesis of 4-trifluoromethyl pyridazines has been developed. Abstract : 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.