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Synthesis 2009(22): 3838-3842  
DOI: 10.1055/s-0029-1217027
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New and Efficient Route for the Synthesis of Naturally Occurring Catecholamines

Roberta Bernini*a, Fernanda Crisantea, Maurizio Barontinia, Giancarlo Fabrizib
a Dipartimento di Agrobiologia e Agrochimica, Università degli Studi della Tuscia, Via S. Camillo De Lellis, 01100 Viterbo, Italy
Fax: +39(761)357242; e-Mail: berninir@unitus.it;
b Dipartimento di Chimica e Tecnologie del Farmaco, Università degli Studi ‘La Sapienza’, P. le A. Moro 5, 00185 Rome, Italy
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Publication History

Received 27 June 2009
Publication Date:
23 September 2009 (online)

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Abstract

Catecholamines, sympathomimetic drugs and adrenergic receptor antagonists, have been prepared by a regioselective oxidation of the corresponding 4-hydroxyphenethylamine derivatives by 2-iodoxybenzoic acid (IBX) in homogeneous as well as in heterogeneous conditions and followed by cleavage of the amino protective group. By using polymer-supported IBX, after the first oxidation, the oxidant can be recovered, regenerated, and efficiently reused for several additional times. An efficient, easy and green procedure for the synthesis of N-(methoxycarbonyl)dopamine, key component of many pharmaceuticals, has also been reported.

Key words

N-(methoxycarbonyl)dopamine - catecholamines - aromatic hydroxylation - 2-iodoxybenzoic acid - polymer-supported IBX

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