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Molecules 2013, 18(2), 1869-1880; doi:10.3390/molecules18021869
Article

Silica-Supported Polyphosphoric Acid in the Synthesis of 4-Substituted Tetrahydroisoquinoline Derivatives

,  and *
Department of Organic Chemistry, University of Plovdiv, 24 Tzar Assen str., 4000 Plovdiv, Bulgaria
* Author to whom correspondence should be addressed.
Received: 19 December 2012 / Revised: 21 January 2013 / Accepted: 22 January 2013 / Published: 1 February 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

We report herein an application of an α-amidoalkylation reaction, as an alternative efficient synthesis of 4-aryl- and 4-methyl-1,2,3,4-tetrahydroisoquinoline derivatives. The amides required for this purpose would result from reaction of aminoacetaldehyde dimethylacetal with different substituted benzenes in polyphosphoric acid, followed by acylation of the obtained amines with different acid chlorides or sulfochlorides. We compared the cyclisation step using conventional (milieu of acetic-trifluoracetic acid = 4:1) and solid supported reagents (SiO2/PPA), as recovered, regenerated and reused without loss of its activity catalyst. We found that in comparison to conventional methods, the yields of the reaction are greater and the reaction time is shorter.
Keywords: 4-substituted tetrahydroisoquinoline; cherylline analogues; α-amidoalkylation reaction; silica-supported polyphosphoric acid (SiO2-PPA) 4-substituted tetrahydroisoquinoline; cherylline analogues; α-amidoalkylation reaction; silica-supported polyphosphoric acid (SiO2-PPA)
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Manolov, S.; Nikolova, S.; Ivanov, I. Silica-Supported Polyphosphoric Acid in the Synthesis of 4-Substituted Tetrahydroisoquinoline Derivatives. Molecules 2013, 18, 1869-1880.

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