Parallel solution-phase synthesis of (Z)-3-(arylamino)-2,3-dehydroalanine derivatives and solid-phase synthesis of fused pyrimidones

Petra Cebasek; Jernej Wagger; David Bevk; Renata Jakse; Jurij Svete; Branko Stanovnik

doi:10.1021/cc034066c

Parallel solution-phase synthesis of (Z)-3-(arylamino)-2,3-dehydroalanine derivatives and solid-phase synthesis of fused pyrimidones

J Comb Chem. 2004 May-Jun;6(3):356-62. doi: 10.1021/cc034066c.

Authors

Petra Cebasek¹, Jernej Wagger, David Bevk, Renata Jakse, Jurij Svete, Branko Stanovnik

Affiliation

¹ Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, 1000 Ljubljana, Slovenia.

PMID: 15132595
DOI: 10.1021/cc034066c

Abstract

N-Protected (Z)-3-(arylamino)-2,3-dehydroalanine esters 5 and 10 were prepared in one step from methyl (Z)-2-acylamino-3-(dimethylamino)prop-2-enoates 3 and 9 and anilines 4 employing a parallel solution-phase synthetic approach. In most cases, analytically pure products 5 and 10 were obtained. On the other hand, a three-step parallel solid-phase synthesis of 2-acetylamino-4H-azino[1,2-x]pyrimidin-4-ones 15 via the polymer-bound methyl (Z)-2-acetylamino-3-(dimethylamino)prop-2-enoate (12) was also developed.