In this paper, we describe a new silver catalysed domino approach to 6-substituted benzoxazino isoquinolines starting from 2-alkynylbenzaldehydes and 1-substituted-(2-aminophenyl)methanols. The strategy is characterized by good reaction yields, and can be performed at room temperature as well as under heating (conventional or dielectric) in different reaction times. Best results have been obtained by using silver complexes of macrocyclic pyridine-containing ligands (PcL) as catalysts. The stereoselectivity of the transformation has been investigated by using chiral reaction partners and chiral catalyst, but unfortunately, modest stereoselectivities has been achieved. On the other hand, this approach represents an alternative synthetic strategy for the preparation of 6-substituted benzoxazino isoquinolines, which are the key scaffold of some compounds endowed of biological activity.

[Ag(PcL)]-Catalysed Domino Approach to 6-Substituted Benzoxazino Isoquinolines / D. Garanzini, V. Pirovano, I. Menghi, G. Celentano, S. Rizzato, E. Rossi, A. Caselli, G. Abbiati. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2020(2020 Jul), pp. 3660-3670. [10.1002/ejoc.202000341]

[Ag(PcL)]-Catalysed Domino Approach to 6-Substituted Benzoxazino Isoquinolines

D. Garanzini
Primo
;
V. Pirovano
Secondo
;
G. Celentano;S. Rizzato;E. Rossi;A. Caselli
Penultimo
;
G. Abbiati
Ultimo
2020-07

Abstract

In this paper, we describe a new silver catalysed domino approach to 6-substituted benzoxazino isoquinolines starting from 2-alkynylbenzaldehydes and 1-substituted-(2-aminophenyl)methanols. The strategy is characterized by good reaction yields, and can be performed at room temperature as well as under heating (conventional or dielectric) in different reaction times. Best results have been obtained by using silver complexes of macrocyclic pyridine-containing ligands (PcL) as catalysts. The stereoselectivity of the transformation has been investigated by using chiral reaction partners and chiral catalyst, but unfortunately, modest stereoselectivities has been achieved. On the other hand, this approach represents an alternative synthetic strategy for the preparation of 6-substituted benzoxazino isoquinolines, which are the key scaffold of some compounds endowed of biological activity.
Alkynes; Pyridine containing ligands; Silver; Domino reactions; Microwaves; Polycyclic N-O Heterocycles
Settore CHIM/06 - Chimica Organica
6-mag-2020
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/733085
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