Diborane (4) derivatives via coupling of amine monobromocyanoboranes: Study of the bromination of amine cyanoborane and molecular structures of the amine dibromocyanoboranes
“…Preparation of Amine Halocyanoboranes. The corresponding amine monobromocyanoboranes and amine dibromocyanoboranes were prepared from the starting amine cyanoboranes as described previously in the literature (Scheme ). , The synthesis of amine fluorocyanoboranes was carried out by reacting the corresponding amine bromocyanoboranes with silver fluoride (AgF) according to a method that was previously described by Shalom et al (Scheme ). 5 Synthesis of Amine Halocyanoboranes a a R 1 , R 2 , and R 3 = alkyl. …”
Section: Resultsmentioning
confidence: 99%
“…46 Compounds 1-6, 25, and 27 were re-synthesized as described in our previously published articles. 37,38 Synthesis of Compounds 8-9,14,16-18, and 28. Me 3 NBH 2 -CN (0.098 g, 1 mmol) was dissolved in 20 mL of dry THF and cooled to -78 °C, and 1.15 mL, 1.5 mmol of 1.3 M s-BuLi/hexane solution was added dropwise.…”
Section: Methodsmentioning
confidence: 99%
“…Me 3 NBH 2 CN was prepared from Me 3 N·HCl and NaBH 3 CN using the literature method . Compounds 1 - 6 , 25 , and 27 were re-synthesized as described in our previously published articles. , …”
A series of new amine cyanoborane derivatives were synthesized and exhibited antifungal activity. A long alkyl chain attached to the nitrogen of the amine cyanoboranes and carboxyboranes enhances antifungal activity. An enhanced activity was also obtained upon the halogenation of the amine cyanoboranes as well as in the presence of C=C double bond at the end of the N-alkyl group. The lead compounds were dimethylundecylamine cyanoborane (C11H23N(CH3)2BH2CN), 9, and its dibromo derivative dimethylundecylamine dibromocyanoborane (C11H23N(CH3)2BBr2CN), 11. The MIC values for the lead compounds against the most important human pathogenic fungi ranged from 16.25 to 32.5 micromol/L and from 10.05 to 79 micromol/L, respectively. Both compounds were found to be relatively safe in intravenous injections to mice, (MTD = 121.9 and 73.1 micromol/kg, respectively) and active against strains that are resistant to fluconazole (a conventional antifungal medicine). These data indicate their potential to become antifungal agents.
“…Preparation of Amine Halocyanoboranes. The corresponding amine monobromocyanoboranes and amine dibromocyanoboranes were prepared from the starting amine cyanoboranes as described previously in the literature (Scheme ). , The synthesis of amine fluorocyanoboranes was carried out by reacting the corresponding amine bromocyanoboranes with silver fluoride (AgF) according to a method that was previously described by Shalom et al (Scheme ). 5 Synthesis of Amine Halocyanoboranes a a R 1 , R 2 , and R 3 = alkyl. …”
Section: Resultsmentioning
confidence: 99%
“…46 Compounds 1-6, 25, and 27 were re-synthesized as described in our previously published articles. 37,38 Synthesis of Compounds 8-9,14,16-18, and 28. Me 3 NBH 2 -CN (0.098 g, 1 mmol) was dissolved in 20 mL of dry THF and cooled to -78 °C, and 1.15 mL, 1.5 mmol of 1.3 M s-BuLi/hexane solution was added dropwise.…”
Section: Methodsmentioning
confidence: 99%
“…Me 3 NBH 2 CN was prepared from Me 3 N·HCl and NaBH 3 CN using the literature method . Compounds 1 - 6 , 25 , and 27 were re-synthesized as described in our previously published articles. , …”
A series of new amine cyanoborane derivatives were synthesized and exhibited antifungal activity. A long alkyl chain attached to the nitrogen of the amine cyanoboranes and carboxyboranes enhances antifungal activity. An enhanced activity was also obtained upon the halogenation of the amine cyanoboranes as well as in the presence of C=C double bond at the end of the N-alkyl group. The lead compounds were dimethylundecylamine cyanoborane (C11H23N(CH3)2BH2CN), 9, and its dibromo derivative dimethylundecylamine dibromocyanoborane (C11H23N(CH3)2BBr2CN), 11. The MIC values for the lead compounds against the most important human pathogenic fungi ranged from 16.25 to 32.5 micromol/L and from 10.05 to 79 micromol/L, respectively. Both compounds were found to be relatively safe in intravenous injections to mice, (MTD = 121.9 and 73.1 micromol/kg, respectively) and active against strains that are resistant to fluconazole (a conventional antifungal medicine). These data indicate their potential to become antifungal agents.
Doubly electrophilic pyrazabole derivatives (pyrazabole = [H2B(-C3N2H3)]2) combined with one equiv. of base effect the ortho-borylation of N-alkyl anilines. Initial studies found that the bis(trifluoromethane)sulfonimide ([NTf2]-) pyrazabole derivative, [H(NTf2)B(-C3N2H3)]2, is...
Cyanoborate chemistry has emerged to an important topic during the last two decades, beginning with two independent reports on the successful synthesis of the tetracyanoborate anion [B(CN) 4 ]in 2000. A wealth of cyanoborate anions with different substituents in addition to CN group(s) bonded to boron, i.e. hydrogen, halogen, aryl, alkenyl, alkyl, perfluoroalkyl, and alkoxy, have been developed, which enable the tuning of properties of compounds and materials based on them. The readily accessible alkali metal cyanoborates are convenient starting materials for the preparation of cyanoborates with various organic, inorganic, and metal cations as well as cyanoborate coordination compounds. A focus has been on low-[a] Julius-Maximilians-Universität Würzburg,
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
