Synthesis and Transformations of di-endo-3-Aminobicyclo-[2.2.2]oct-5-ene-2-carboxylic Acid Derivatives

Molecules

Márta Palkó¹  Pál Sohár¹ 

[1] ¹Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary ²Institute of Chemistry, Eötvös Lóránd University, H-1518 Budapest, POB 32, Hungary

关键词: hydroxy-b-amino acids;    cyclization;    heterocycles;    retro Diels-Alder reaction;    microwave;   

DOI  :  10.3390/molecules16097691

来源: mdpi

【 摘 要 】

all-endo-3-amino-5-hydroxybicyclo[2.2.2]octane-2-carboxylic acid (13) and all-endo-5-amino-6-(hydroxymethyl)bicyclo[2.2.2]octan-2-ol (10) were prepared via dihydro-1,3-oxazine or g-lactone intermediates by the stereoselective functionalization of an N-protected derivative of endo-3-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acid (2). Ring closure of b-amino ester 4 resulted in tricyclic pyrimidinones 15 and 16. The structures, stereochemistry and relative configurations of the synthesized compounds were determined by IR and NMR.

【 授权许可】

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