A1 Refereed original research article in a scientific journal
A novel solid support for derivatization and subsequent N-alkylation of secondary amines: Preparation of N-alkylated 5- and 6-alkoxy-1,2,3,4-tetrahydroisoquinolines via Mitsunobu reaction
Authors: Heinonen P, Lonnberg H
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Publication year: 1997
Journal:: Tetrahedron Letters
Journal name in source: TETRAHEDRON LETTERS
Journal acronym: TETRAHEDRON LETT
Volume: 38
Issue: 49
First page : 8569
Last page: 8572
Number of pages: 4
ISSN: 0040-4039
DOI: https://doi.org/10.1016/S0040-4039(97)10286-6
Abstract
A hydroxymethylated polystyrene resin has been converted to its vinylsulfonylethyl ether (1) by DBU catalyzed addition of the hydroxy groups to divinyl sulfone. The support obtained was used to convert 5- and 6-(tetrahydropyran-2-yloxy)-1,2,3,4-tetrahydroisoquinolines to a set of N-alkylated tetrahydroisoquinolines bearing various 5- and 6-alkoxy substituents (5a-m). The synthesis involved attachment of the starting material to the support by Michael addition, acid-catalyzed removal of the tetrahydropyranyl protection, Mitsunobu etherification, quaternarization with alkyl amines, and release in solution with diisopropylethylamine. (C) 1997 Elsevier Science Ltd.
A hydroxymethylated polystyrene resin has been converted to its vinylsulfonylethyl ether (1) by DBU catalyzed addition of the hydroxy groups to divinyl sulfone. The support obtained was used to convert 5- and 6-(tetrahydropyran-2-yloxy)-1,2,3,4-tetrahydroisoquinolines to a set of N-alkylated tetrahydroisoquinolines bearing various 5- and 6-alkoxy substituents (5a-m). The synthesis involved attachment of the starting material to the support by Michael addition, acid-catalyzed removal of the tetrahydropyranyl protection, Mitsunobu etherification, quaternarization with alkyl amines, and release in solution with diisopropylethylamine. (C) 1997 Elsevier Science Ltd.
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