通过膦介导的邻位磺酰基酰肼环脱水反应合成肼基砜内酯
Synthesis of Hydrazonyl Sultones via Phosphine-Mediated Cyclodehydration of Vicinal Sulfo-acyl Hydrazides.
作者信息
Borade Balasaheb R, Fang Ming, Lin Qing
机构信息
Department of Chemistry, State University of New York at Buffalo, Buffalo, New York 14260-3000, United States.
出版信息
Org Lett. 2024 Oct 4;26(39):8239-8243. doi: 10.1021/acs.orglett.4c02687. Epub 2024 Sep 23.
Abstract
We report a phosphine-mediated cyclodehydration procedure for the facile synthesis of -aryl/alkyl-substituted hydrazonyl sultones, a class of bioorthogonal reagents, from the readily prepared vicinal sulfo-acyl hydrazides in moderate to good yields. The aqueous stability and bioorthogonal reactivity of these hydrazonyl sultones toward bicyclo[6.1.0]non-4-yn-9-ylmethanol were investigated, revealing key structural requirements for hydrazonyl sultones to possess balanced stability and reactivity.
摘要
我们报道了一种由膦介导的环脱水方法，可从易于制备的邻位磺酰基酰肼中简便地合成一类生物正交试剂——芳基/烷基取代的肼基磺内酯，产率适中至良好。研究了这些肼基磺内酯对双环[6.1.0]壬-4-炔-9-基甲醇的水稳定性和生物正交反应性，揭示了肼基磺内酯具有平衡稳定性和反应性的关键结构要求。
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