Isochromene is an interesting oxygen-containing heterocycle characterizing different synthetic bioactive molecules and natural products. The isochromene core can be synthetized exploiting a regioselective 6-endo-dig domino approach starting from 2-alkynylbenzaldehydes and suitable nucleophiles, under transition metal catalysis, able to activate the triple bond. Most employed nucleophiles are oxygen- and carbon-based compounds, otherwise nitrogen-containing nucleophiles usually bring to the formation of isoquinoline derivatives, through the formation of the corresponding imine intermediate. Herein we report the first synthesis of 1-amino substituted isochromene derivatives starting from different 2-alkynylbenzaldehydes exploiting the features of electron-poor anilines and PcL silver complex catalysis. A series of 1-arylaminoisochromene was prepared, differently substituted in 3 position with alkyl, cycloalkyl, aryl or heteroaryl moiety. Reaction conditions, scope and limitation or the approach and a plausible mechanism of the reaction will be presented and discussed.

Synthesis of 1-Aminoisochromenes through reactions of 2-alkynylbenzaldehydes with electron-poor anilines promoted by [Ag(PcL)] catalysts / D. Garanzini, E. Brambilla, V. Pirovano, E. Rossi, G. Abbiati. ((Intervento presentato al 1. convegno I Virtual Symposium on Pericyclic Reactions and Synthesis of Carbo- and Heterocyclic Systems tenutosi a On-line nel 2020.

Synthesis of 1-Aminoisochromenes through reactions of 2-alkynylbenzaldehydes with electron-poor anilines promoted by [Ag(PcL)] catalysts

D. Garanzini;E. Brambilla;V. Pirovano;E. Rossi;G. Abbiati
2020-11-24

Abstract

Isochromene is an interesting oxygen-containing heterocycle characterizing different synthetic bioactive molecules and natural products. The isochromene core can be synthetized exploiting a regioselective 6-endo-dig domino approach starting from 2-alkynylbenzaldehydes and suitable nucleophiles, under transition metal catalysis, able to activate the triple bond. Most employed nucleophiles are oxygen- and carbon-based compounds, otherwise nitrogen-containing nucleophiles usually bring to the formation of isoquinoline derivatives, through the formation of the corresponding imine intermediate. Herein we report the first synthesis of 1-amino substituted isochromene derivatives starting from different 2-alkynylbenzaldehydes exploiting the features of electron-poor anilines and PcL silver complex catalysis. A series of 1-arylaminoisochromene was prepared, differently substituted in 3 position with alkyl, cycloalkyl, aryl or heteroaryl moiety. Reaction conditions, scope and limitation or the approach and a plausible mechanism of the reaction will be presented and discussed.
2-alkynylbenzaldehydes; silver; TM catalysis; isochromenes; domino reaction;
Settore CHIM/06 - Chimica Organica
Centro Interuniversitario di Ricerca sulle Reazioni Pericicliche e Sintesi di Sistemi Etero e Carbociclici
Società Chimica Italiana
https://sites.unimi.it/cirp/?p=666
Synthesis of 1-Aminoisochromenes through reactions of 2-alkynylbenzaldehydes with electron-poor anilines promoted by [Ag(PcL)] catalysts / D. Garanzini, E. Brambilla, V. Pirovano, E. Rossi, G. Abbiati. ((Intervento presentato al 1. convegno I Virtual Symposium on Pericyclic Reactions and Synthesis of Carbo- and Heterocyclic Systems tenutosi a On-line nel 2020.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/818171
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