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Ultrasound Assisted Pictet–Spengler Synthesis of Tetrahydro‐β‐Carboline Derivatives
Authors:Gisela C Muscia  Leonardo O De María  Graciela Y Buldain  Silvia E Asís
Institution:Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Ciudad Autónoma de Buenos Aires, Argentina
Abstract:The synthesis of twelve tetrahydro‐β‐carboline derivatives 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h , 3i , 3j , 3k , 3l prepared via the Pictet–Spengler reaction is described. The reaction of tryptamine and a variety of arylaldehydes were carried out under ultrasonic irradiation and trifluoracetic acid catalysis at room temperature. These tetrahydro‐β‐carbolines have been synthesized in higher yields and shorter reaction times compared to the conventional method. Moreover, the reaction proceeded successfully even employing arylaldehydes with electron‐donating or electron‐attracting substituents which did not react under conventional method.
Keywords:
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