Journal of Organic Chemistry p. 8864 - 8872 (2017)
Update date:2022-08-04
Topics: NMR Analysis
Huang, Adrian
Wo, Kellie
Lee, So Yeun Christine
Kneitschel, Nika
Chang, Jennifer
Zhu, Kathleen
Mello, Tatsiana
Bancroft, Laura
Norman, Natalie J.
Zheng, Shao-Liang
A systematic study of the N-substitution reactions of 3-substituted pyrazoles under basic conditions has been undertaken. Regioselective N1-alkylation, -arylation, and -heteroarylation of 3-substituted pyrazoles have been achieved using K2CO3-DMSO. The regioselectivity is justified by the DFT calculations at the B3LYP/6-31G??(d) level. A consistent steric effect on chemical shift has been observed for N-alkyl pyrazole analogues. Twenty-five X-ray crystallographic structures have been obtained to confirm the regiochemistry of the major products.
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