2‐Oxabicyclo[2.1.1]hexanes: Synthesis, Properties, and Validation as Bioisosteres of <i>ortho</i>‐ and <i>meta</i>‐Benzenes
Vadym V. Levterov, Yaroslav Panasiuk, Oleh Shablykin, Oleksandr Stashkevych, Kateryna Sahun, Artur Rassokhin, Iryna V. Sadkova, Dmytro Lesyk, Anna Anisiforova, Yuliia Holota, Petro Borysko, Iryna Bodenchuk, Nataliya M. Voloshchuk, Pavel K. Mykhailiuk
Abstract
We have developed a general and practical approach towards 2-oxabicyclo[2.1.1]hexanes with two and three exit vectors via an iodocyclization reaction. The obtained compounds have been easily converted into the corresponding building blocks for use in medicinal chemistry. 2-Oxabicyclo[2.1.1]hexanes have been incorporated into the structure of five drugs and three agrochemicals, and validated biologically as bioisosteres of ortho- and meta-benzenes.
Topics & Concepts
PhilosophyOrganic Chemistry Cycloaddition ReactionsOxidative Organic Chemistry ReactionsChemistry and Chemical Engineering