4.5 Article

Catalyst-free, one-pot expeditious synthesis of polyhydroquinolines and 2-amino-4H-chromenes

Journal

RESEARCH ON CHEMICAL INTERMEDIATES
Volume 48, Issue 8, Pages 3429-3447

Publisher

SPRINGER
DOI: 10.1007/s11164-022-04763-0

Keywords

Polyhydroquinolines; Chromene; Dimedone; Multicomponent; Catalyst-free

Funding

  1. Department of Science and Technology, India, India (WOS-A)
  2. All India Council for Technical Education, QIP, New Delhi, India
  3. Rajeev Gandhi Science and Technology Mission, Govt. of Maharashtra, India

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This study presents a rapid and efficient method for synthesizing polyhydroquinolines using the Hantzsch reaction and 2-amino-4H-chromene derivatives. The method is catalyst-free and uses ethanol: water (1:1) at room temperature and 90 degrees Celsius. It demonstrates the ability to handle diverse substrates with different functional groups, including ketones. Furthermore, this method offers economical and environmentally friendly advantages with shorter reaction time, simple workup procedure, no catalyst, and excellent yields.
The present work highlights a rapid, efficient, eco-friendly protocol for synthesizing one-pot polyhydroquinolines via Hantzsch reaction and 2-amino-4H-chromene derivatives under catalyst-free condition. The present mild and greener method uses ethanol: water (1:1) without catalyst at R.T. and 90 degrees C. The structurally diverse substrates were selected to ascertain the ability of the current approach to handle different functional groups, including ketones as one of the substrates. The current methodology is economical and environmentally friendly for the three and four-component reaction of aliphatic, acyclic, aromatic, heterocyclic aldehydes in shorter reaction time, simple workup procedure, no catalyst with excellent yields, and high atom efficiency are the added advantages of this protocol. [GRAPHICS] .

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