Synthesis of Substituted 1,2,3,4-Tetrahydro-6-methyl-2-oxo-5-pyrimidinecarboxylic Acid Esters: The Biginelli Condensation Revisited

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

“…Mono‐ or unsubstituted ureas are generally used to access the corresponding 1( N )‐mono(un)substituted pyrimidines. Over the last few decades, this reaction has been significantly improved in terms of yield, scope, and durability thanks to the many variations and modifications developed (including multistep methodologies) [5,6,13–15] . However, despite these achievements, control of site‐selectivity on the pyrimidine ring remains a synthetic challenge.…”

“…[3][4][5] Known since the early 1990s as Biginelli pyrimidines, this family of compounds has successfully led to a number of drug candidates. [6][7][8][9][10][11][12] However, general synthetic strategies to construct the 3,4-dihydropyrimidin-2(1H)-one ring are still limited to a few disconnection approaches. The most attractive and widely used method is undeniably the classic three-component Biginelli cyclocondensation (Scheme 1a).…”

Topologically Driven Pore/Surface Engineering in a Recyclable Microporous Metal–Organic Vessel Decorated with Hydrogen-Bond Acceptors for Solvent-Free Heterogeneous Catalysis

“…To the best of our knowledge, such a combination in the same catalyst is very rare. For a proof of concept, we chose to consider the Biginelli reaction for the one-pot synthesis of dihydropyrimidinones, which are known for their numerous therapeutic benefits such as antihypertensive, anticancer, antimicrobial, antihyperglycemic, antiarrhythmic, anti-inflammatory, analgesic, antibacterial, anti-HIV, and antitubercular activities. , The conventional Biginelli reaction involves the use of strong acids, such as concentrated HCl, which comes with its disadvantages of making the reaction messy and making the isolation of products cumbersome, giving low reaction yields. − To overcome this, several improvisations have been made in the past (Scheme ) to increase the efficacy of the reaction involving Lewis acids such as halides and triflate salts of different metal ions, inorganic compounds like alumina and silica, ionic liquids, various polymeric supports, etc. , Most of the studies stress on activating the electrophilic aldehydic center by the use of Lewis acids based on either coordinatively unsaturated metal centers or bare metal acetates or triflates of a variety of metal ions screened throughout the periodic table. Apart from this, many protonic acids like H 2 SO 4 , p -toluenesulfonic acid, HBF 4 , molybdophosphoric acid, phenylboronic acid, boric acid, acetic acid, trifluoro acetic acid, trifluoromethane sulfonic acid, etc., have been used for this reaction .…”

One-pot two step synthesis of 5-cyano-dihydropyrimidinones using polyphosphate ester

“…This compound was later found to induce a phenotype in cells similar to the Eg5 inhibitor Monastrol. 3 The original synthesis of 2 described by Atwal et al [4][5][6] involved a four step process utilizing a Knoevenagel condensation affording 2 in a 10% overall yield. To explore the SAR of this potential series of cytotoxic agents, a general and high yielding route was required.…”