Synthesis of maleimide-functionalized carboranes and their utility in Michael addition reactions

Carborane maleimides were prepared in good yields through the thermal cyclization of maleamic acids prepared by the reaction of 3-amino-o-carborane with maleic or 3-bromomaleic anhydrides, respectively. The selective reactivity of synthesized maleimides towards S-nucleophiles was demonstrated. As a result a series of boronated thiosuccinimide- or thiomaleimide-substituted compounds including boron rich ones was obtained and fully characterized. Furthermore the opportunity of variation with substitution patterns may lead to the development of potential candidates for biological applications or the development of new materials.

Automated summary

Carborane maleimides were synthesized with good yields through thermal cyclization of maleamic acids prepared from the reaction of 3-amino-o-carborane with maleic or 3-bromomaleic anhydrides. The selective reactivity of synthesized maleimides towards S-nucleophiles was demonstrated, leading to the development of potential candidates for biological applications or new materials with variation in substitution patterns.