Title of article
Synthesis of pyrimidinyl arylglycines through subsequent Mitsunobu and Petasis reactions
Author/Authors
David Font، نويسنده , , Montserrat Heras، نويسنده , , José M. Villalgordo، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2008
Pages
10
From page
5226
To page
5235
Abstract
The synthesis of highly functionalized pyrimidinyl arylglycines is presented. The highlight in our synthetic sequence includes selective O-alkylation of 2-(benzylsulfanyl)-4(3H)-pyrimidinones with N-Boc β-aminoalcohols under Mitsunobu conditions, Petasis reaction with glyoxylic acid and phenylboronic acid and nucleophilic ipso-substitution of the activated sulfur with morpholine. The unexpected spontaneous Smiles rearrangement of several pyrimidinyl amines is also discussed.
Keywords
Nucleophilic ipso-substitution , Arylglycines , Pyrimidines , Mitsunobu reaction , Smiles rearrangement , Petasis reaction
Journal title
Tetrahedron
Serial Year
2008
Journal title
Tetrahedron
Record number
1094132
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