Zhong Zhenhao, Ma Tsz-Kan, White Andrew J P, Bull James A
Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London W12 0BZ, U.K.
Org Lett. 2024 Feb 16;26(6):1178-1183. doi: 10.1021/acs.orglett.3c04274. Epub 2024 Feb 2.
Sulfoximines and pyrazoles are both important motifs in medicinal compounds. Here we report the synthesis and reactivity of sulfoximine diazo compounds as new reagents for the incorporation of sulfoximines. The use of -silyl sulfoximines enabled formation of monosubstituted diazo compounds. Their application is demonstrated in a [3 + 2] cycloaddition with alkynes to form pyrazole sulfoximines in a new combination of these important chemotypes. Further derivatization of the pyrazole sulfoximines is demonstrated, including silyl deprotection to form unprotected pyrazolesulfoximines.
砜亚胺和吡唑都是药物化合物中的重要结构单元。在此,我们报告了砜亚胺重氮化合物作为引入砜亚胺的新试剂的合成及反应活性。使用 - 硅基砜亚胺能够形成单取代重氮化合物。它们的应用在与炔烃的 [3 + 2] 环加成反应中得到了证明,从而以这些重要化学类型的新组合形成吡唑砜亚胺。还展示了吡唑砜亚胺的进一步衍生化,包括硅基脱保护以形成未保护的吡唑砜亚胺。