The synthesis of 3-substituted 1-methylpyrrolo[1,2-a]pyrazines and 3-substituted isoquinolines was achieved by the intramolecular cyclisation of 2-acetyl-1-propargylpyrroles and 2-alkynylbenzaldehydes, respectively, in the presence of ammonia under microwave heating. The tandem imination/annulation of 2-alkynylbenzaldehydes was easily accomplished under standard conditions, while TiCl4 was used to achieve pyrrolo[1,2-a]pyrazines. The reaction mechanism and the regioselectivity were discussed on the basis of theoretical calculations and spectroscopic data
Microwave-Promoted Synthesis of N-Heterocycles by Tandem Imination/Annulation of gamma- and delta-Ketoalkynes in the Presence of Ammonia / M. Alfonsi, M. Dell’Acqua, D. Facoetti, A. Arcadi, G. Abbiati, E. Rossi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2009:17(2009), pp. 2852-2862. [10.1002/ejoc.200900014]
Microwave-Promoted Synthesis of N-Heterocycles by Tandem Imination/Annulation of gamma- and delta-Ketoalkynes in the Presence of Ammonia
M. Dell’AcquaSecondo
;D. Facoetti;G. Abbiati
Penultimo
;E. RossiUltimo
2009
Abstract
The synthesis of 3-substituted 1-methylpyrrolo[1,2-a]pyrazines and 3-substituted isoquinolines was achieved by the intramolecular cyclisation of 2-acetyl-1-propargylpyrroles and 2-alkynylbenzaldehydes, respectively, in the presence of ammonia under microwave heating. The tandem imination/annulation of 2-alkynylbenzaldehydes was easily accomplished under standard conditions, while TiCl4 was used to achieve pyrrolo[1,2-a]pyrazines. The reaction mechanism and the regioselectivity were discussed on the basis of theoretical calculations and spectroscopic dataFile | Dimensione | Formato | |
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