Affiliation:
1. Department of Organic Chemistry, Faculty of Chemistry and Geosciences Vilnius University Naugarduko St. 24 Vilnius LT-03225
2. Department of Bioinformatics Institute of Biotechnology Life Sciences Center Vilnius University Saulėtekio St. 7 Vilnius LT-10257
Abstract
AbstractThe van Leusen reaction utilizes p‐toluenesulfonylmethyl isocyanide as a versatile synthon for constructing nitrogen‐containing heterocycles, such as oxazoles, imidazoles, thiazoles, and pyrroles. In this study, the van Leusen imidazole reaction, employed for synthesizing potential Hsp90 inhibitors, yielded unexpected side products containing novel condensed tricycles, specifically 3a,8b‐dihydro‐1H‐benzofuro[2,3‐d]imidazoles. The mechanism behind the formation of this unprecedented fragment was further analyzed through quantum mechanical calculations and experimental investigations of the reaction outcome under different reaction conditions and with various substituents. Additionally, the stabilities of the products were evaluated.