Organophotoredox-Catalyzed C–H Alkylation of Imidazoheterocycles with Malonates: Total Synthesis of Zolpidem

Narendra R. Chaubey; Anant R. Kapdi; Biswanath Maity

doi:10.1055/s-0040-1706103

Synthesis, Table of Contents

Synthesis 2021; 53(08): 1524-1530
DOI: 10.1055/s-0040-1706103

paper

Organophotoredox-Catalyzed C–H Alkylation of Imidazoheterocycles with Malonates: Total Synthesis of Zolpidem

Authors

Narendra R. Chaubey ∗

^aInstitute of Chemical Technology, Department of Chemistry, Nathalal Parekh Road, Matunga, Mumbai 400019, Maharashtra, India
Anant R. Kapdi

^aInstitute of Chemical Technology, Department of Chemistry, Nathalal Parekh Road, Matunga, Mumbai 400019, Maharashtra, India
Biswanath Maity

^bTranslational Cell Biology Unit, Centre of Biomedical Research, Raibareli Road, Lucknow, Uttar-Pradesh 226014, India

Abstract

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Abstract

Organophotocatalytic C–H bond functionalization has attracted a lot of attention in the past several years due to the possibility of catalyzing reactions in a metal- and peroxide-free environment. Continuing on these lines, an organophotoredox-catalyzed C–H functionalization of imidazo[1,2-a]pyridines and related heterocycles with bromomalonates under mild conditions is reported, providing excellent yields of the products at room temperature. This is the first report involving malonates as coupling partners leading to the synthesis of a range of functionalized products including total synthesis of zolpidem, a sedative-hypnotic drug molecule.

Key words

organophotoredox - C–H functionalization - imidazoheterocycles - zolpidem - drug prejudice

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