A simple and direct palladium‐catalyzed aminocarbonylation of 5‐iodo‐1,2,3‐triazoles backbone for the incorporation of an amide functional group is presented. The approach is based on the palladium catalyzed carbonylative coupling reaction of iodo‐triazole with different amines employing formic acid and sulfuric acid as CO source (Morgan's reaction) to provide the 1,2,3‐triazole‐5‐carboxamides in good to excellent yields. The important features of this methodology include short reaction time, high yields, the use of dimethyl carbonate as a sustainable solvent, and the use of efficient alternative source of carbon monoxide, avoiding pressurized cylinder. The methodology described herein for the synthesis of 1,4,5‐trisubstituted 1,2,3‐triazole‐5‐carboxamides, can offers an alternative path for functionalization of other heterocycles.
Enantiomerically enriched diaryl, aryl heteroaryl, and diheteroaryl alcohols are an important family of compounds known for their biological properties. Moreover, these molecules are highly privileged scaffolds used as building blocks for the synthesis of pharmaceutically relevant products. This short review provides background on the enantioselective arylation and heteroarylation of carbonyl compounds, as well as, the most significant improvements in this field with special emphasis on the application of organometallic reagents.1 Introduction2 Background on the Enantioselective Synthesis of Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols3 Organozinc Reagents4 Organolithium Reagents5 Grignard Reagents6 Organoaluminum Reagents7 Organotitanium Reagents8 Organobismuth Reagents9 Miscellaneous10 Conclusion
A new
catalytic protocol for the synthesis of selenoesters from
aryl iodides and diaryl diselenides has been developed, where formic
acid was employed as an efficient, low-cost, and safe substitute for
toxic and gaseous CO. This protocol presents a high functional group
tolerance, providing access to a large family of selenoesters in high
yields (up to 97%) while operating under mild reaction conditions,
and avoids the use of selenol which is difficult to manipulate, easily
oxidizes, and has a bad odor. Additionally, this method can be efficiently
extended to the synthesis of thioesters with moderate-to-excellent
yields, by employing for the first time diorganyl disulfides as precursors.
This work aims the synthesis of amidino pyrazolines by the cyclocondensation reaction between 3-(hetero)aryl-1-(2-hydroxyphenyl)enones and aminoguanidine hydrochloride under sonochemical conditions. Thirteen new compounds were synthesized in 15-83% of yield after sonication for 30 min without purification by chromatography. Furthermore, antimicrobial activities of the synthesized compounds were investigated by in vitro minimum inhibitory concentration (MIC) in a panel of four bacterial strains and four Candida yeasts. As result, the 5-(4-bromophenyl)-3-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride was identified as the most active against gram-positive S. aureus and E. faecalis with MIC of 7.8 µg mL −1 , similar to the value showed by chloramphenicol, which was used as standard.
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