RESUMO
BACKGROUND AND OBJECTIVE: The objective of our work was to establish a facile and scalable synthesis of imidazopyridone for further use in medicinal chemistry applications. An easy synthesis of a core scaffold will enable the medicinal chemistry community to use imidazopyridone as a privileged scaffold in new chemical entity (NCE) synthesis. MATERIALS AND METHODS: The synthesis was achieved from commercially available and cheap raw materials like amino acetonitrile hydrochloride or commercially available guanidine. RESULTS: Simple transformation starting from amino acetonitrile hydrochloride leads to the synthesis of a versatile imidazo [1, 5-a] pyrimidine-2-(1H)-one core structure. Using suitable functionalized starting materials, a set of NCEs were synthesized to demonstrate the application of the developed synthetic scheme. Similarly, guanidine was also used to synthesize a regioisomer of imidazopyridone in moderate to good yields. CONCLUSION: We demonstrate the synthesis of two different regio-isomers of imidazopyrimidinone using simple chemical transformations. Its application in synthesizing NCEs has also been exhibited in the present work.
RESUMO
Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7 a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical alpha,alpha-disubstituted aldehydes to beta-nitroalkenes. When this asymmetric transformation was catalyzed by organocatalyst 7 f, the desired Michael adducts were obtained in high chemical yields, with high to excellent stereoselectivities (up to 98:2 diastereomeric ratio (d.r.) and 99 % enantiomeric excess (ee)). The scope of the catalytic system was expanded to encompass various aldehydes and ketones as the donor sources. The synthetic application was demonstrated by the synthesis of a tetrasubstituted-cyclohexane derivative from (S)-citronellal, with high stereoselectivity.
