Display options
Cite
Chelucci G, Porcheddu A. Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization. Chem Rec. 2016;17(2):200-216doi: 10.1002/tcr.201600083.
Chelucci, G., & Porcheddu, A. (2017). Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization. Chemical record (New York, N.Y.), 17(2), 200-216. https://doi.org/10.1002/tcr.201600083
Chelucci, Giorgio, and Porcheddu, Andrea. "Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization." Chemical record (New York, N.Y.) vol. 17,2 (2017): 200-216. doi: https://doi.org/10.1002/tcr.201600083
Chelucci G, Porcheddu A. Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization. Chem Rec. 2017 Feb;17(2):200-216. doi: 10.1002/tcr.201600083. Epub 2016 Aug 15. PMID: 27524555.
Copy Download .nbib Format: NLM
Share it on

Chem Rec. 2017 Feb;17(2):200-216. doi: 10.1002/tcr.201600083. Epub 2016 Aug 15.

Synthesis of Quinolines via a Metal-Catalyzed Dehydrogenative N-Heterocyclization.

Chemical record (New York, N.Y.)

Giorgio Chelucci, Andrea Porcheddu

Affiliations

  1. Dipartimento di Agraria, Università di Sassari, Viale Italia 39, I-07100, Sassari, Italy.
  2. Università di Cagliari, Dipartimento di Scienze Chimiche e Geologiche, Cittadella Universitaria, SS 554 bivio per Sestu, I-09042, Monserrato (Ca), Italy.

PMID: 27524555 DOI: 10.1002/tcr.201600083

Abstract

Efficient ruthenium-, rhodium-, palladium-, copper- and iridium-catalysed methodologies have been recently developed for the synthesis of quinolines by the reaction of 2-aminobenzyl alcohols with carbonyl compounds (aldehydes and ketones) or the related alcohols. The reaction is assumed to proceed via a sequence involving initial metal-catalysed oxidation of 2-aminobenzyl alcohols to the related 2-aminobenzaldehydes, followed by cross aldol reaction with a carbonyl compound under basic conditions to afford α,β-unsaturated carbonyl compounds. These aldehydes or ketones can be also generated in situ via dehydrogenation of the related primary and secondary alcohols. In the final step cyclodehydration of the α,β-unsaturated carbonyl compound intermediates gives quinolines. Good yields of quinolines were also obtained by reacting 2-nitrobenzyl alcohols and secondary alcohols in the presence of a ruthenium catalyst. Finally, aniline derivatives afforded also a useful access to quinolines by the reaction with 1,3-propanediol or 3-amino-1-propanol, or in a three-component reaction with benzyl alcohol and aliphatic alcohols.

© 2017 The Chemical Society of Japan & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Alcohols; aldehydes; dehydrogenation; ketones; metal complexes; quinolones

Publication Types