- [Ag(PcL)]-Catalysed Domino Approach to 6-Substituted Benzoxazino Isoquinolines
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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 catalysts, but unfortunately, modest stereoselectivities have 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.
- Abbiati, Giorgio,Caselli, Alessandro,Celentano, Giuseppe,Garanzini, Davide,Menghi, Ilaria,Pirovano, Valentina,Rizzato, Silvia,Rossi, Elisabetta
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- One-pot synthesis of dihydrobenzo[4,5][1,3]oxazino[2,3-A] isoquinolines via a silver(I)-catalyzed cascade approach
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An efficient approach for the synthesis of biologically interesting fused tetracyclic isoquinolines in high yields and with a broad substrate scope has been developed. The strategy features an AgNO3 catalyzed 'one-pot' cascade process involving formation of two new C-N bonds and one new C-O bond.
- Jiang, Baifeng,Zhou, Yu,Kong, Qingya,Jiang, Hualiang,Liu, Hong,Li, Jian
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p. 814 - 831
(2013/04/10)
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