Abstract
A novel synthetic pathway to approach 3-(imino)isoindolin-1-ones by the Co-catalyzed cyclization reaction of 2-bromobenzamides with carbodiimides has been developed. This catalytic reaction can tolerate a variety of substituents and provide corresponding products in moderate yields for most cases. According to the literature, the reaction mechanism is proposed through the formation of a five-membered aza-cobalacycle complex, which carries out the following reaction subsequence, including nucleophilic addition and substitution, to furnish the desired structures.
Highlights
3-(Imino)isoindolin-1-one, an interesting N-heterocycle with two unsymmetrically unsaturated C-X functional groups on the five-membered indole core, has attracted attention from chemists in various fields due to its uncommon structure. This unique structure has enhanced the difficulty of its synthetic pathways; only limited reports have described synthetic methods to approach the derivatives of 3-(imino)isoindolin-1one [1,2,3,4,5,6,7,8,9,10,11,12,13,14]
The first-row transition-metal complexes exhibit comparably higher economic efficiency, and our continuing studies on cobalt-catalyzed coupling reactions [25], as well as the experiences in cyclization reactions [26,27,28,29,30,31,32,33,34,35], encouraged us to attempt the synthesis of diverse N-heterocyclic scaffolds by using the five-membered cobalacycle intermediate and switching different cyclization partners (Scheme 2)
We carried out the cobalt-catalyzed cyclization reaction of 2-bromobenzamides with
Summary
3-(Imino)isoindolin-1-one, an interesting N-heterocycle with two unsymmetrically unsaturated C-X functional groups on the five-membered indole core, has attracted attention from chemists in various fields due to its uncommon structure. A variety of late-transition-metals have been shown to possess the ability to form this intermediate for further transformations [5,7,15,16,17,18,19,20,21,22,23,24], which have been commonly indicated to construct six- or five-membered N-heterocyclic structures via the 1,2- or 1,1-insertion of molecules containing multiple bonds For those revealed catalysts, the first-row transition-metal complexes exhibit comparably higher economic efficiency, and our continuing studies on cobalt-catalyzed coupling reactions [25], as well as the experiences in cyclization reactions [26,27,28,29,30,31,32,33,34,35], encouraged us to attempt the synthesis of diverse N-heterocyclic scaffolds by using the five-membered cobalacycle intermediate and switching different cyclization partners (Scheme 2).
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