2008
DOI: 10.1055/s-0028-1087383
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Synthesis of 1-Methylbenzimidazoles from Carbonitriles

Abstract: The NaH-mediated N-methylbenzimidazole formation starting from carbonitriles and N-methyl-1,2-phenylenediamine is reported to be a procedure compatible with acid-labile acetal protective groups within the starting materials. Products were further converted in Suzuki, Sonogashira, Heck and Buchwald-Hartwig reactions.

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Cited by 6 publications
(1 citation statement)
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“…Another approach for the synthesis of 2-substituted BnZ was published by Cui et al in 2012 for producing 1,2-phenylenediamines and triacyloxyborane intermediates, which were produced via the interaction between carboxylic acids [E] and borane-THF, to yield 2-substituted BnZ [ 13 ]. N-methyl-1,2-phenylenediamine, sodium hydride, and carbonitriles [F] were used as the starting ingredients by Sluiter and Christoffers in 2009 [ 14 ]. Wray synthesized [ 1 ] 1H-indazoles from common arylamino oximes in 2010 in the presence of several bases, but the synthesis of BnZ was only improved by one base, i.e., triethylamine [G] [ 15 ].…”
Section: Synthesis Of Benzimidazolementioning
confidence: 99%
“…Another approach for the synthesis of 2-substituted BnZ was published by Cui et al in 2012 for producing 1,2-phenylenediamines and triacyloxyborane intermediates, which were produced via the interaction between carboxylic acids [E] and borane-THF, to yield 2-substituted BnZ [ 13 ]. N-methyl-1,2-phenylenediamine, sodium hydride, and carbonitriles [F] were used as the starting ingredients by Sluiter and Christoffers in 2009 [ 14 ]. Wray synthesized [ 1 ] 1H-indazoles from common arylamino oximes in 2010 in the presence of several bases, but the synthesis of BnZ was only improved by one base, i.e., triethylamine [G] [ 15 ].…”
Section: Synthesis Of Benzimidazolementioning
confidence: 99%