Synthesis of Ester-Substituted Indolizines from 2-Propargyloxypyridines and 1,3-Dicarbonyls.

Carolyn E Anderson, Haleigh I Bos, Daniel M Dreher, Colin T Hartgerink, Chase J Scholtens, Richard J Staples

The Journal of organic chemistry 2022 Aug 05

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Two new complementary Au(I)-catalyzed methods for the preparation of ester-substituted indolizines from easily accessible 2-propargyloxypyridines and either acetoacetates or dimethyl malonate are reported. These reactions tolerate a wide range of functionality, allowing for diversification at three distinct positions of the product (R, R1, R2). For electron-poor substrates, the highest yields are observed upon reaction with acetoacetates, while neutral and electron-rich substrates give higher yields upon treatment with dimethyl malonate.

Citation

Carolyn E Anderson, Haleigh I Bos, Daniel M Dreher, Colin T Hartgerink, Chase J Scholtens, Richard J Staples. Synthesis of Ester-Substituted Indolizines from 2-Propargyloxypyridines and 1,3-Dicarbonyls. The Journal of organic chemistry. 2022 Aug 05;87(15):10241-10249