Base-controlled regioselective functionalization of 2-(indolizin-1-yl)-4,4-dimethyl-4,5-dihydrooxazole

Over the last few years, indolizines have received great attention due to its successful application in many fields, such as agrochemicals, pharmaceuticals and in medicinal chemistry. This success is because indolizine scaffolds have been found in many bioactive natural products, drug molecules and organic fluorescent materials.1 More recently, indolizines have proved to be versatile intermediates in countless organic transformations. Consequently, many synthetic strategies have been developed for the construction of new functionalized indolizines. Among the most important methodologies are Tschitschibabin reaction, 1,3-dipolar cycloadditions, cycloisomerization and intramolecular cyclization. In this work, we have explored the directed metalation of 2-(indolizin-1-yl)-4,4-dimethyl-4,5-dihydrooxazole using n-BuLi and TMPMg∙LiCl, through this methodology 10 new di-functionalized indolizines have been prepared.