1983
DOI: 10.1002/jhet.5570200232
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Synthesis of 2‐oxo and 6‐hydroxylated benzimidazole analogs of DOPA as potential norepinephrine antagonists

Abstract: The synthesis of benzimidazolone analogs of DOPA and α‐methyl‐DOPA and of the benzimidazole and benzimidazolone analogs of 6‐hydroxy‐DOPA is reported. These compounds showed a moderate amount of dopamine β‐hydroxylase and tyrosine hydroxylase inhibitory activity but did not significantly alter tissue catacholamine levels.

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Cited by 4 publications
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“…Diamine 28 was converted into amino acid esters 8 − 10 as shown in Scheme . Benzotriazole amino ester 8 was obtained in 80% yield and 99.6% ee (two steps, from 27 ) by the reaction of 28 (X = OAc) with NaNO 2 . The reaction of diamine 28 (X = Cl) and carbonyl diimidazole afforded benzoimidazolone amino ester 9 in 50% yield (2 steps, from 27 ) .…”
Section: Resultsmentioning
confidence: 99%
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“…Diamine 28 was converted into amino acid esters 8 − 10 as shown in Scheme . Benzotriazole amino ester 8 was obtained in 80% yield and 99.6% ee (two steps, from 27 ) by the reaction of 28 (X = OAc) with NaNO 2 . The reaction of diamine 28 (X = Cl) and carbonyl diimidazole afforded benzoimidazolone amino ester 9 in 50% yield (2 steps, from 27 ) .…”
Section: Resultsmentioning
confidence: 99%
“…The ee of amino ester 9 was not determined. Finally, 2-methylbenzimidazole amino ester 10 was obtained in 81% yield and 97.6% ee (2 steps, from 27 ) by heating diamine 28 (X = OAc) in AcOH at reflux for 4 h …”
Section: Resultsmentioning
confidence: 99%
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