2010
DOI: 10.1002/jhet.385
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Preparation of 2,4,5‐triarylimidazol‐4‐ols and their stereoselective rearrangement by 1,5‐phenyl migration

Abstract: in Wiley InterScience (www.interscience.wiley.com).Lophine hydroperoxides underwent base-triggered 1,5-phenyl migration in DMSO to afford imidazolones in high yields, instead of amidines with chemiluminescence (CL). The corresponding imidazolols were believed to intermediates and they were successfully obtained by treating the peroxides with DMSO without the base. The diminished CL was because of the reduction of the hydroperoxides with DMSO. The imidazolols subsequently underwent smooth base-mediated rearrang… Show more

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Cited by 7 publications
(2 citation statements)
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“…It should be mentioned that observed transformations include a rare example of phenyl group migration from phosphorus to a carbon dyad in spite of the fact that phenyl group migration proceeds as by radical, so by the ionic mechanism is well known and studied for the cases of migration in dyads CC , SiC , and PN .…”
Section: Resultsmentioning
confidence: 99%
“…It should be mentioned that observed transformations include a rare example of phenyl group migration from phosphorus to a carbon dyad in spite of the fact that phenyl group migration proceeds as by radical, so by the ionic mechanism is well known and studied for the cases of migration in dyads CC , SiC , and PN .…”
Section: Resultsmentioning
confidence: 99%
“…Kimura and co-workers report a stereoselective 1,5phenyl migration on several imidazolols upon addition of base in DMSO, producing 5,5-diarylated imidazol-4-ones (ee > 90%). 102 In nature, the pinacol rearrangement is used to convert 2′-deoxyguanosine to a spiroimidazolone. 103 This reaction was found to occur naturally through single-electron oxidation under basic conditions ( pH > 8) and can also take place in acetic acid with m-chloroperbenzoic acid (mCPBA) or dimethyldioxirane (DMDO).…”
Section: Heterocyclic Conversion/rearrangementsmentioning
confidence: 99%