Substituted 1-aminopyrroles are easily accessible by means of iron-catalyzed cascade reaction that requires as starting materials the solely 1,2-diaza-1,3-dienes. Mechanistically, the formal [3 + 2] cyclodimerization is hypothesized to proceed through a [4 + 2] cyclodimerization of 4-substitued 1,2-diaza-1,3-dienes followed by intramolecular ring closure to fused diaziridin-pyrrolines whose successive opening results in a ring contraction process with consequent generation of the pyrrole moiety. The presence of activated hydrogen in the terminal position of the azo-enic moiety is crucial for the success of the synthesis.

FeCl3-catalyzed formal [3 + 2] cyclodimerization of 4-carbonyl-1,2-diaza-1,3-dienes

Giacomo Mari
Project Administration
;
Matteo Corrieri
Membro del Collaboration Group
;
Lucia De Crescentini;Gianfranco Favi
Membro del Collaboration Group
;
Stefania Santeusanio
Membro del Collaboration Group
;
Fabio Mantellini
Conceptualization
2021-01-01

Abstract

Substituted 1-aminopyrroles are easily accessible by means of iron-catalyzed cascade reaction that requires as starting materials the solely 1,2-diaza-1,3-dienes. Mechanistically, the formal [3 + 2] cyclodimerization is hypothesized to proceed through a [4 + 2] cyclodimerization of 4-substitued 1,2-diaza-1,3-dienes followed by intramolecular ring closure to fused diaziridin-pyrrolines whose successive opening results in a ring contraction process with consequent generation of the pyrrole moiety. The presence of activated hydrogen in the terminal position of the azo-enic moiety is crucial for the success of the synthesis.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11576/2690545
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