Compared reactivity of a β-aminothiol and a β-Aminoalcohol towards Phenylglyoxal

In agreement with a previous theoretical statement, ( R)- N-methyl phenylglycinol and ( R)- N-methyl phenylglycinethiol react with phenylglyoxal to give respectively six and five-membered heterocycles. As predicted by previous calculations, N-methyl phenylglycinol and N-methyl phenylglycinethiol rea...

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Bibliographic Details
Published inTetrahedron letters Vol. 34; no. 44; pp. 7061 - 7062
Main Authors Agami, Claude, Couty, François, Prince, Béatrice, Venier, Olivier
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 29.10.1993
Elsevier
Subjects
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
Sulfur nitrogen heterocycle
Five membered ring
Ketoaldehyde
Aminoalcohol
Cyclization
Six membered ring
Aminothiol
Chemical reactivity
Oxygen nitrogen heterocycle
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Summary:In agreement with a previous theoretical statement, ( R)- N-methyl phenylglycinol and ( R)- N-methyl phenylglycinethiol react with phenylglyoxal to give respectively six and five-membered heterocycles. As predicted by previous calculations, N-methyl phenylglycinol and N-methyl phenylglycinethiol react with phenylglyoxal to give six and five-membered cyclized products.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)61598-8