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Challenge N- versus O-six-membered annulation: FeCl3-catalyzed synthesis of heterocyclic N,O-aminals.


ABSTRACT: A new class of heterocyclic N,O-aminal and hemiaminal scaffolds was successfully obtained by means of a three-component reaction (3-CR) of 1,2-diaza-1,3-dienes (DDs), α-aminoacetals and iso(thio)cyanates. These stable imine surrogates are generated from key-substituted (thio)hydantoin intermediates through selective FeCl3-catalyzed intramolecular N-annulation.

SUBMITTER: Mari G 

PROVIDER: S-EPMC11216082 | biostudies-literature | 2024

REPOSITORIES: biostudies-literature

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Challenge <i>N</i>- versus <i>O</i>-six-membered annulation: FeCl<sub>3</sub>-catalyzed synthesis of heterocyclic <i>N</i>,<i>O</i>-aminals.

Mari Giacomo G   De Crescentini Lucia L   Favi Gianfranco G   Mantellini Fabio F   Olivieri Diego D   Santeusanio Stefania S  

Beilstein journal of organic chemistry 20240626


A new class of heterocyclic <i>N</i>,<i>O</i>-aminal and hemiaminal scaffolds was successfully obtained by means of a three-component reaction (3-CR) of 1,2-diaza-1,3-dienes (DDs), α-aminoacetals and iso(thio)cyanates. These stable imine surrogates are generated from key-substituted (thio)hydantoin intermediates through selective FeCl<sub>3</sub>-catalyzed intramolecular <i>N</i>-annulation. ...[more]

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