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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

Narendra R. Chaubey  ∗
a   Institute of Chemical Technology, Department of Chemistry, Nathalal Parekh Road, Matunga, Mumbai 400019, Maharashtra, India
,
Anant R. Kapdi
a   Institute of Chemical Technology, Department of Chemistry, Nathalal Parekh Road, Matunga, Mumbai 400019, Maharashtra, India
,
Biswanath Maity
b   Translational Cell Biology Unit, Centre of Biomedical Research, Raibareli Road, Lucknow, Uttar-Pradesh 226014, India
› Author AffiliationsDr. Narendra R. Chaubey acknowledges the Research Fellowship (F. No. 45/15/2019-BIO/BMS) from Indian Council of Medical Research, Delhi, India.
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706606.
  • Supporting Information


Publication History

Received: 28 October 2020

Accepted after revision: 29 October 2020

Article published online:
02 December 2020

© 2020. Thieme. All rights reserved

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