5 years ago

Regioselective Synthesis, NMR, and Crystallographic Analysis of N1-Substituted Pyrazoles

Regioselective Synthesis, NMR, and Crystallographic Analysis of N1-Substituted Pyrazoles
Shao-Liang Zheng, Laura Bancroft, Natalie J. Norman, Jennifer Chang, So Yeun Christine Lee, Adrian Huang, Nika Kneitschel, Kathleen Zhu, Kellie Wo, Tatsiana Mello
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01006

DOI: 10.1021/acs.joc.7b01006

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