Alkylquinolines and Arylquinolines

Claret, P. A.; Osborne, Alan G.

doi:10.1002/9780470187036.ch1

Cited by 3 publications

References 1,140 publications

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Tetrazole compounds. 9. A new approach to tetrazolyl‐substituted quinoline derivatives

Fischer

1994

Journal of Heterocyclic Chem

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The acid‐catalyzed reaction of 1‐aryl‐5‐(2‐dimethylaminovinyl)‐1H‐tetrazoles 2 with arylamines suitably functionalized in the ortho‐position resulted in Z‐configurated transamination products which were cyclized to novel 3‐tetrazolylquinolines by the action of sodium ethoxide. Thus, on reacting 2 with 2‐aminoacetophenone or 2‐aminobenzophenone, respectively, the 2‐[2‐(1‐aryl‐1H‐tetrazol‐5‐yl)vinyl‐amino]aryl ketones 3a‐g were obtained, the cyclization of which gave 4‐substituted 3‐(1‐aryl‐1H‐tetrazol‐5‐yl)quinolines 4. In the case of the transamination products 3h‐1, prepared from 2 and methyl anthranilate, the ring closure afforded 3‐(1‐aryl‐1H‐tetrazol‐5‐yl)‐1H‐quinolin‐4‐ones 5. Starting from 2 and anthranilonitrile 4‐amino‐3‐(1‐aryl‐1H‐tetrazol‐5‐yl)quinolines 10 were obtained via the corresponding intermediates 9.

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Tetrazole compounds. 9. A new approach to tetrazolyl‐substituted quinoline derivatives

Fischer

1994

Journal of Heterocyclic Chem

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The Literature of Heterocyclic Chemistry, Part III

Беленький

1988

Advances in Heterocyclic Chemistry Volume 44

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A Pummerer Reaction-Enabled Modular Synthesis of Alkyl Quinoline-3-carboxylates and 3-Arylquinolines from Amino Acids

Chen

Tang

et al. 2023

J. Org. Chem.

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Concise synthesis of functionalized quinolines has received continuous research attention owing to the biological importance and synthetic potential of bicyclic N-heterocycles. However, synthetic routes to the 2,4-unsubstituted alkyl quinoline-3-carboxylate scaffold, which is an important motif in drug design, remain surprisingly limited, with modular protocols that proceed from readily available materials being even more so. We herein report an acidic I2–DMSO system that converts readily available aspartates and anilines into alkyl quinoline-3-carboxylate. This method can be extended to a straightforward synthesis of 3-arylquinolines by simply replacing the aspartates with phenylalanines. Mechanistic studies revealed that DMSO was activated by HI via a Pummerer reaction to provide the C1 synthon, while the amino acid catabolized to the C2 synthon through I2-mediated Strecker degradation. A formal [3 + 2 + 1] annulation of these two concurrently generated synthons with aniline was responsible for the selective formation of the quinoline core. The synthetic utility of this protocol was illustrated by the efficient synthesis of human 5-HT4 receptor ligand. Moreover, an unprecedented chemoselective synthesis of 2-deuterated, 3-substituted quinoline, featuring this reaction, has been established.

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Alkylquinolines and Arylquinolines

Cited by 3 publications

References 1,140 publications

Tetrazole compounds. 9. A new approach to tetrazolyl‐substituted quinoline derivatives

Tetrazole compounds. 9. A new approach to tetrazolyl‐substituted quinoline derivatives

The Literature of Heterocyclic Chemistry, Part III

A Pummerer Reaction-Enabled Modular Synthesis of Alkyl Quinoline-3-carboxylates and 3-Arylquinolines from Amino Acids

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