2479-64-3Relevant articles and documents
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Brotherton,R.J.,Steinberg,H.
, p. 4632 - 4634 (1961)
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Synthesis of Functionalized 1,3,2-Benzodiazaborole Cores Using Bench-Stable Components
Davies, Geraint H. M.,Molander, Gary A.
, p. 3771 - 3779 (2016/05/24)
The azaborine motif provides a unique opportunity to develop core isosteres by inserting B-N units in place of C-C bonds within aromatic scaffolds, creating new pseudoaromatic building blocks that retain comparable structural features. Previous synthetic routes to the 1,3,2-benzodiazaborole core have used organoboron dichlorides and boronic acids as the boron precursors. The transformation developed herein utilizes entirely bench stable starting materials, including organotrifluoroborates, enabling a wider array of substrate analogues under facile reaction conditions. Furthermore, physical, structural, and electronic properties of these compounds were explored computationally to understand the influence of the B-N replacement on the structure, aromaticity, and isosteric viability of these analogues.
Boric acid-catalyzed direct condensation of carboxylic acids with benzene-1,2-diamine into benzimidazoles
Maras, Nenad,Kocevar, Marijan
experimental part, p. 1860 - 1874 (2011/12/02)
The applicability of boric acid catalysis for the direct condensation of carboxylic acids with benzene-1,2-diamine to give 2-substituted benzimidazoles was investigated. It was found that catalytic amounts (5-10 mol-%) of boric acid efficiently promote the cyclocondensation of aliphatic carboxylic acids in refluxing toluene. In addition, the relatively neutral conditions allow the use of acid-sensitive substrates and give rise to specific transformations and selectivities that are not observed with some classical methods. Benzoic acids were found to be less reactive than aliphatic acids and thus require refluxing xylene for better efficiency. Phenylboronic acid was found to be inactive as a catalyst due to its rapid consumption by condensation with benzene-1,2-diamine to give a 2-phenylbenzodiazaborole. Copyright