Microwave-induced Synthesis of N-Substituted 1-Alkyl and 1-Aryl 3-Aminoisoquinolines

CÁNEPA, A.S.; BRAVO R. D.; MENDEZ, L.J.; BRAVO R. D.; VILLALBA M.L.; CÁNEPA, A.S.; MENDEZ, L.J.; VILLALBA M.L.

LETTERS IN ORGANIC CHEMISTRY

BENTHAM SCIENCE PUBL LTD

Lugar: Oak Park; Año: 2017 vol. 14 p. 8 - 13

1570-1786

Abstract: Background: Aminoisoquinolines are an important class of heterocyclic compounds. Thesecompounds present a wide range of pharmacological properties including antimalaric, anticonvulsantand anti-inflammatory. Although several preparation routes may be found in the literature for the preparationof these compounds, many of these methods present difficulties, including laborious isolationmethods, drastic conditions and extended reaction times.Methods: The synthesis of N-substituted 1-alkyl and 1-aryl- 3-aminoisoquinolines is developed throughthe reaction of 2-acylphenylacetonitriles with amines under microwave irradiation conditions. The reactionswere performed in ethanol as a solvent without the use of catalyst. In parallel, these reactions wereperformed under identical conditions of temperature using P2O5/SiO2 as a catalyst in different amounts.Results: A series of N-substituted 1-alkyl and 1-aryl- 3-aminoisoquinolines were synthesized using microwaveirradiation with as high selectivity, short reaction times and without the use of catalyst. The useof P2O5/SiO2 as catalyst under microwave irradiation conditions was not effective for these reactions.Conclusion: The results show an efficient method for the synthesis of N-substituted 1-alkyl and 1-aryl-3-aminoisoquinolines by the reaction of 2-acylphenylacetonitriles with amines using microwave irradiation.Some important advantages for this method include a strong decrease in reaction time, a good selectivity,and the absence of catalyst, with simplicity in operation and a benefit to the environment.