Highly Regioselective Addition of Organozinc Reagents to 2‐Oxo‐1,2‐dihydropyrimidine‐5‐carboxylates Activated by BF₃·OEt₂: Synthesis of 2‐Oxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylates

Abstract

The C—4 position of these compounds has an important influence on their calcium channel blocking activity.

Hydroaminoalkyl Functionalization of Pyrimidin‐2(1H)‐ones by Visible Light Organophotocatalysis: A Radical Approach to Biginelli‐Type Dihydropyrimidines

“…A second approach (Scheme 1b) is based on the addition of Cnucleophile onto the C=CÀ C=N endocyclic system of the pyrimidin-2(1H)-one scaffold, either at the C4position (direct addition to the C=N bond) or at the C6-position (1,4-conjugate addition). [16][17][18][19][20][21][22] This method offers interesting molecular diversity by varying the nature of the stabilized carbanions (i. e., alkynide, enolate, nitronate, or cyanide). [23][24][25][26][27][28] In this case, however, regioselectivity is difficult to control due to various factors (i. e. substrate, reagent, reaction con-ditions) and the reversible nature of nucleophilic addition.…”

“…However, despite these achievements, control of site‐selectivity on the pyrimidine ring remains a synthetic challenge. A second approach (Scheme 1b) is based on the addition of C‐nucleophile onto the C=C−C=N endocyclic system of the pyrimidin‐2(1 H )‐one scaffold, either at the C4‐position (direct addition to the C=N bond) or at the C6‐position (1,4‐conjugate addition) [16–22] . This method offers interesting molecular diversity by varying the nature of the stabilized carbanions (i. e., alkynide, enolate, nitronate, or cyanide) [23–28] .…”