Tandem Synthesis of Tetrahydropyrroloquinazolines and Related Polyannular Scaffolds
Haley M Carlson1, R Adam Mosey1
1Lake Superior State University, 650 W. Easterday Ave., Sault Sainte Marie, Michigan 49783, United States.
Abstract:
A Tf2O-mediated tandem synthesis of tetrahydropyrroloquinazolines from amino amides and aldehydes has been developed in which both heterocyclic rings of the scaffold are assembled in a single pot. An alkyl tether linking the amide and amine functionalities acts as a carbon bridge to form saturated rings about the core amidine moiety, thereby facilitating the installation of diverse fused cycloalkyl and bicyclic ring systems. The reaction also extends to the formation of the indoloquinazolinone scaffold.
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