Base-Catalyzed One-Pot Synthesis of Indolizine-1-carboxylates Tethered to 2-Aroyl Benzofurans and Benzothiophenes

Herein, we report a base-catalyzed one-pot synthesis of indolizine-1-carboxylates tethered to 2-aroyl benzofurans and benzothiophenes from 2-pyridin-2-ylacetates, DMF-DMA, and 2-aroyl-benzofuran/benzothiophene-3-methyl bromides. This protocol provides access to diverse indolizine derivatives in moderate to good yields under simple conditions. A broad range of substituents on both the benzofuran/benzothiophene and pyridine-2-ylacetate components was tolerated well, and gram-scale synthesis was achieved without chromatographic purification. In addition, postsynthetic Suzuki coupling of the bromine-containing products enabled the construction of highly conjugated indolizine-benzofuran architectures.