An Efficient Synthesis of Pyrimidines from β-Amino Alcohols

Abstract

[reaction: see text] Pyrimidinones 3 were chemoselectively reduced by using metal-catalyzed hydrogenation and stereoselectively substituted by various nucleophiles. Starting from beta-amino alcohols 1, the overall process allows efficient access to substituted pyrimidines 4 and 6.

Synthesis of aromatic heterocycles

“…The five membered ring can then be cleaved by reaction with nucleophiles, the products being 1,6-disubstituted pyrimidine-2,4-diones 248. 360, 361 The reactions of amidines with vinyl trifluoroacetyl ketones produced 2,6-disubstituted 4-trifluoroacetylpyrimidines in good yield. The use of phosphorus oxychloride and manganese dioxide as dehydrating and oxidising agents allowed the reactions to be carried out as a "one pot" procedure.…”

Parallel Solid-Phase Synthesis and Structural Characterization of a Library of Highly Substituted Chiral 1,3-Oxazolidines

“…1,3-Oxazolidines are remarkably versatile molecules having found use as chiral auxiliaries, , as intermediates for more complex chiral heterocycles, − and as prodrugs for improving the pharmacokinetic profile of certain β -amino alcohol pharmacophores . They are ideally suited as scaffolds for combinatorial library generation because they have a rigid core that possesses four sites for the incorporation of diversity elements and can be synthesized with a high degree of chiral integrity (Figure A).…”

An Efficient Synthesis of a New Series of Acyclonucleosides Starting from β-Amino Alcohols

“…Majority of reactions concerning the synthesis of such acyclonucleosides had been made by regioselective N -alkylations of the purine ring system . We have developed a more convergent method starting from β-amino alcohols (Scheme ) that allows the efficient synthesis of a great variety of nucleosides 3 .

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