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DOI: 10.1055/a-2370-6625
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Transition-Metal-Free Approach for the Synthesis of N-Arylated Piperidones and their Ketals from Ketene Dithioacetals

Satya Narayan Sahu
a   Department of Chemistry, Swami Atmanand Government English Medium Model College Ambikapur, 497001, India
,
Ranjay Shaw
b   Department of Chemistry, GLA University, Mathura, U.P., 281406, India
,
Ismail Althagafi
c   Department of Chemistry, Faculty of Science, Umm Al-Qura University, Makkah, 21955, Saudi Arabia
,
Ramendra Pratap∗
d   Department of Chemistry, University of Delhi, Delhi, 110007, India
› Author AffiliationsWe thank the University of Delhi for providing research funding under IoE, FRP grant, and USIC. R.P. thanks CSIR, New Delhi for providing the research funding [02(469)/23/EMR-II].
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Dedicated to Professor H. Ila on her 80th birthday

Abstract

N-Arylated piperidones are present as pharmacophores in many pharmaceuticals and serve as useful precursors for the construction of important new molecules. We have developed a transition-metal-free, cost-effective, and mild approach for the synthesis of N-(hetero)arylated piperidones and their ketals by using ketals of piperidones and 2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitriles as precursors. The desired products were obtained in two steps: amination of the 2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitrile from piperidone, followed by ring transformation using a suitable nucleophile source. We have successfully tethered functionalized dihydrophenanthrenes, hydrobenzo[c]phenanthrenes, and benzoquinolines to piperidinone moieties under transition-metal-free conditions.

Key words

ketene dithioacetals - piperidone - dihydrophenanthrenes - chromenes - ring transformation - cyanoacetamides

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2370-6625.
  • Supporting Information


Publication History

Received: 11 May 2024

Accepted after revision: 22 July 2024

Accepted Manuscript online:
22 July 2024

Article published online:
21 August 2024

© 2024. Thieme. All rights reserved

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