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Recent Syntheses of 1,2,3,4-Tetrahydroquinolines, 2,3-Dihydro-4(1H)-quinolinones and 4(1H)-Quinolinones using Domino Reactions

Journal

MOLECULES
Volume 19, Issue 1, Pages 204-232

Publisher

MDPI AG
DOI: 10.3390/molecules19010204

Keywords

domino reaction; tandem reaction; cascade reaction; 1,2,3,4-tetrahydroquinoline; 2,3-dihydro-4(1H)-quinolinone; 4(1H)-quinolinone; heterocycle synthesis; drug synthesis

Funding

  1. NIH [GM 54256]
  2. Oklahoma Center for the Advancement of Science and Technology [HR1-035, HR01-015]
  3. Oklahoma State University
  4. OSU College of Arts and Sciences
  5. NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R15GM054256] Funding Source: NIH RePORTER

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A review of the recent literature is given focusing on synthetic approaches to 1,2,3,4-tetrahydroquinolines, 2,3-dihydro-4(1H)-quinolinones and 4(1H)-quinolinones using domino reactions. These syntheses involve: (1) reduction or oxidation followed by cyclization; (2) SNAr-terminated sequences; (3) acid-catalyzed ring closures or rearrangements; (4) high temperature cyclizations and (5) metal-promoted processes as well as several less thoroughly studied reactions. Each domino method is presented with a brief discussion of mechanism, scope, yields, simplicity and potential utility.

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