Reaction of α,α-Dibromo Oxime Ethers with Grignard Reagents:  Alkylative Annulation Providing a Pyrimidine Core

Abstract

A convergent synthesis of a pyrimidine core has been achieved. Treatment of alpha,alpha-dibromo oxime ethers, which are easily derived from the corresponding esters, with a variety of Grignard reagents provides trisubstituted pyrimidines in good yields. This new method offers an easy access to functionalized pyrimidines.

Electrochemical study of catechols in the presence of 4,6-dihydroxy-2-methylpyrimidine

“…Pyrimidines are an important class of heteroaromatic compounds and have widespread applications from pharmaceuticals to materials. A number of pyrimidines are known to have antimicrobial and antitumor activities [15][16][17][18], and a number of benzofuran derivatives are known to have biological activities and to be active in anticancer agent research [19,20]. The importance of these compounds has encouraged their use to investigate the electrochemical oxidation of catechols in the presence of 4,6-dihydroxy-2-methylpyrimidine as a nucleophile and the synthesis of some new compounds from benzofuro [2,3-d] pyrimidines.…”

New Strategies for the Synthesis of Pyrimidine Derivatives

“…[31] Aryl a,a-dibromo oxime ethers can be prepared by O-methyl hydroxylamine hydrogen chloride condensation with a,a-dibromo ketones. Oximes 63 react with a Grignard reagent to afford intermediates 65-68.…”

“…Alkylative annulation strategy for pyrimidine synthesis. [31] Scheme 20. One-pot synthesis of pyrimidines 73 using iminophosphoranes 70.…”

Exploration of the Chemistry and Biological Properties of Pyrimidine as a Privilege Pharmacophore in Therapeutics

“…Furthermore, the prebiotic synthesis of nucleic acid bases is a central issue in the RNA-world hypothesis, one of the main proposals for the origin of life, based on the self-assembly of nucleic acid monomers (Ruiz-Mirazo et al, 2014). Possible scenarios for the synthesis of nucleic acids are still under debate and despite the abiotic synthesis of several nucleobases, the relevance of these syntheses to the origin of life is not well established (Kakiya et al, 2002). Pyrimidine core is found as the inner skeleton in the nucleic acid components; uracil, thymine and cytosine.…”