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Synthesis of Functionalized1,3,2-Benzodiazaborole Cores Using Bench-Stable Components

View Article: PubMed Central - PubMed

ABSTRACT

Theazaborine motif provides a unique opportunity to develop coreisosteres by inserting B–N units in place of C=C bondswithin aromatic scaffolds, creating new pseudoaromatic building blocksthat retain comparable structural features. Previous synthetic routesto the 1,3,2-benzodiazaborole core have used organoboron dichloridesand boronic acids as the boron precursors. The transformation developedherein utilizes entirely bench stable starting materials, includingorganotrifluoroborates, enabling a wider array of substrate analoguesunder facile reaction conditions. Furthermore, physical, structural,and electronic properties of these compounds were explored computationallyto understand the influence of the B–N replacement on the structure,aromaticity, and isosteric viability of these analogues.

No MeSH data available.


B–N isosterismfor C=C bonds.
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fig1: B–N isosterismfor C=C bonds.

Mentions: The ability to createisosteric compounds that alter both the bioavailabilityand reactivity of molecules without significantly modifying the geometricalshape (isostructural) or the electronic distribution (isoelectronic)of that within the parent structure molecule provides a great advantagefor drug development1 and other chemistry-orientedapplications.2 To that end, B–Nisosterism for a carbon–carbon double bond (Figure 1) affords an opportunity tocreate new core isosteric building blocks for aromatic systems (azaborines).Since the initial synthesis of borazine, a completely inorganic isostereof benzene and the first member of the azaborine class,3 a whole range of azaborines have been prepared.4a,4b Further analysis of these cores revealed their unique spectroscopic4c and medicinal properties.4d−4f


Synthesis of Functionalized1,3,2-Benzodiazaborole Cores Using Bench-Stable Components
B–N isosterismfor C=C bonds.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4862404&req=5

fig1: B–N isosterismfor C=C bonds.
Mentions: The ability to createisosteric compounds that alter both the bioavailabilityand reactivity of molecules without significantly modifying the geometricalshape (isostructural) or the electronic distribution (isoelectronic)of that within the parent structure molecule provides a great advantagefor drug development1 and other chemistry-orientedapplications.2 To that end, B–Nisosterism for a carbon–carbon double bond (Figure 1) affords an opportunity tocreate new core isosteric building blocks for aromatic systems (azaborines).Since the initial synthesis of borazine, a completely inorganic isostereof benzene and the first member of the azaborine class,3 a whole range of azaborines have been prepared.4a,4b Further analysis of these cores revealed their unique spectroscopic4c and medicinal properties.4d−4f

View Article: PubMed Central - PubMed

ABSTRACT

Theazaborine motif provides a unique opportunity to develop coreisosteres by inserting B–N units in place of C=C bondswithin aromatic scaffolds, creating new pseudoaromatic building blocksthat retain comparable structural features. Previous synthetic routesto the 1,3,2-benzodiazaborole core have used organoboron dichloridesand boronic acids as the boron precursors. The transformation developedherein utilizes entirely bench stable starting materials, includingorganotrifluoroborates, enabling a wider array of substrate analoguesunder facile reaction conditions. Furthermore, physical, structural,and electronic properties of these compounds were explored computationallyto understand the influence of the B–N replacement on the structure,aromaticity, and isosteric viability of these analogues.

No MeSH data available.