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Gary W Breton

Explore the profile of Gary W Breton including associated specialties, affiliations and a list of published articles. Areas
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Recent Articles
1.
Breton G, Martin K
Molecules . 2024 Sep; 29(17). PMID: 39274916
We have previously demonstrated that an appropriately substituted four-membered-ring 1,2-diazacyclobutene is a useful compound in organic synthesis for the introduction of strained 1,2-diazetidine rings. In order to further explore the...
2.
Breton G, Martin K, Bowron Jr J, Bacsa J
J Org Chem . 2023 Jun; 88(13):9157-9166. PMID: 37364258
Dynamic covalent chemistry (DCvC) is a powerful means by which to rapidly prepare complex structures from simple molecular building blocks. Effective DCvC behavior is contingent upon the reversibility of covalent...
3.
Breton G, Martin K
J Org Chem . 2020 Jul; 85(16):10865-10871. PMID: 32698582
Dynamic covalent chemistry (DCvC) describes systems in which readily reversible bond formation allows for control of product distributions by straightforward manipulation of reaction conditions (e.g., changes in temperature, solvent, concentration,...
4.
Doiron J, Le C, Bacsa J, Breton G, Martin K, Aller S, et al.
ChemMedChem . 2020 May; 15(18):1720-1730. PMID: 32385907
Although the 1,2,3-triazole is a commonly used amide bioisostere in medicinal chemistry, the structural implications of this replacement have not been fully studied. Employing X-ray crystallography and computational studies, we...
5.
Breton G, Hahn L, Martin K
Acta Crystallogr C Struct Chem . 2019 Sep; 75(Pt 9):1208-1212. PMID: 31484807
Tetrahydrotetrazoles are five-membered-ring heterocycles containing four contiguous saturated nitrogen atoms. Very few examples of such compounds have been reported in the literature. Our previous attempt at the synthesis of a...
6.
Doiron J, Le C, Ody B, Brace J, Post S, Thacker N, et al.
Chemistry . 2019 Jan; 25(14):3662-3674. PMID: 30650214
The 1,2,3-triazole has been successfully utilized as an amide bioisostere in multiple therapeutic contexts. Based on this precedent, triazole analogues derived from VX-809 and VX-770, prominent amide-containing modulators of the...
7.
Breton G, Martin K
Acta Crystallogr C Struct Chem . 2018 May; 74(Pt 5):558-563. PMID: 29726464
Tetrahydrotetrazoles are a little-explored class of five-membered heterocycles with four contiguous singly-bonded N atoms. Recent work in our labs has demonstrated that urazole radicals are amenable to N-N bond formation...
8.
Martin K, Breton G
Acta Crystallogr C Struct Chem . 2017 Sep; 73(Pt 9):660-666. PMID: 28872061
Nitrogen-centered urazole radicals exist in equilibrium with tetrazane dimers in solution. The equilibrium established typically favors the free-radical form. However, 1-arylurazole radicals bearing substituents at the ortho position favor the...
9.
Singh S, Das A, Breton G
J Phys Chem A . 2016 Jul; 120(31):6258-69. PMID: 27429098
The n → π* interaction is a weak but important noncovalent interaction present in biomolecules and other compounds. Complexes between 7-azaindole and 2,6-difluorinated pyridines were demonstrated earlier to interact not...
10.
Breton G, Suroviec A
J Org Chem . 2015 Dec; 81(1):206-14. PMID: 26649733
The reaction of N-methyl-1,2,4-triazoline-3,5-dione (MeTAD) with anisole in the presence of trifluoroacetic acid affords unexpected disubstituted urazole products instead of the expected monosubstituted urazole as typically observed in the reactions...