氮杂-醌甲基化物促进氮杂双环[1.1.0]丁烷通过应变释放驱动转化为功能化氮杂环丁烷。
Aza--Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized Azetidines.
作者信息
Singh Bandana, Sasmal Pujan, Taites Aaron, Hazra Subhadeep, Saha Jaideep
机构信息
Department of Biological and Synthetic Chemistry, Centre of Biomedical Research, Lucknow 226014, India.
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali 160062, India.
出版信息
Org Lett. 2024 Nov 8;26(44):9558-9563. doi: 10.1021/acs.orglett.4c03577. Epub 2024 Oct 25.
A strategy for activating azabicyclo[1.1.0]butane (ABB) with generated aza--quinone methide, promoted by HFIP, is reported. This unified activation, strain-release-driven N/C3-functionalization, features a new means to prepare functionalized azetidines from ABB. Additionally, the newly installed motif on azetidine nitrogen could be forged into an indoline Pd-catalyzed hydroamination, leveraging access to medicinally relevant scaffolds.
报道了一种在六氟异丙醇（HFIP）促进下，通过生成氮杂-醌甲基化物来活化氮杂双环[1.1.0]丁烷（ABB）的策略。这种统一的活化，即应变释放驱动的N/C3官能化，是一种从ABB制备官能化氮杂环丁烷的新方法。此外，氮杂环丁烷氮上新安装的基团可以通过钯催化的氢胺化反应转化为二氢吲哚，从而获得与药物相关的支架。
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