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Updated: Jun 21, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Efficient and highly selective synthesis of enantiopure cis- or trans-3,4-disubstituted
José M Concellón1, Paula Tuya, Virginia del Solar
1Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Spain. jmcg@uniovi.es
Abstract:
An efficient synthesis of enantiopure 3,4-disubstituted 1,2,3,4-tetrahydroisoquinolines, by treatment of readily available (2R,1'S)- or (2S,1'S)-2-(1-aminoalkyl)epoxides with H(3)PO(4).BF(3) complex, under mild reaction conditions, is reported. Both enantiopure diastereoisomers (3S,4S)- and (3S,4R)-3-alkyl-4-hydroxymethyl-1,2,3,4-tetrahydroisoquinolines were available starting from the suitable syn- or anti-aminoepoxide, respectively. A mechanism based on an intramolecular Friedel-Crafts-type reaction has been proposed to explain these results.
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