The synthesis of quinoline‐ and isoquinolinecarboxaldehydes

Wommack, J. B.; Barbee, T. G.; Thoennes, D. J.; McDonald, Mark A.; Pearson, D. E.

doi:10.1002/jhet.5570060217

Cited by 26 publications

(3 citation statements)

References 10 publications

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“…To achieve reasonable conversions of the dimethylquinolinecarbonyl chlorides, 12 and 13, to the diazo ketones, it was necessary to use a large excess (20-fold or more) of CH2N3 and long reaction times (24 hr or more) at 25°. 5-Bromo-8-methyl-3-phenylquinoline (26).…”

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confidence: 99%

3-Phenyl-5-quinolinemethanol antimalarials

Makriyannis¹,

Js²,

Jw³

1973

J. Med. Chem.

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confidence: 99%

3-Phenyl-5-quinolinemethanol antimalarials

Makriyannis¹,

Js²,

Jw³

1973

J. Med. Chem.

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“…Nucleophilic addition is a competing reaction in the preparation of lithioquinolines and isoquinolines via metal-halogen exchange, however the use of low temperatures allow metal-halogen exchange at both pyridine [58] and benzene ring positions [59] in quinolines, and the isoquinoline-1-[60] and 4-positions, [61] subsequent reaction with electrophiles generating C-substituted products (Figure 31).…”

Section: Metal-halogen Exchangementioning

confidence: 99%

The Chemistry of Benzo and Carbocyclic Derivatives of Pyridine

Adesina¹

2023

Exploring Chemistry With Pyridine Derivatives

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The chemistry of pyridine and its derivatives is of considerable importance in the synthesis of intermediates leading to biologically active compounds and novel materials. Generally, derivatives of pyridine are stable and relatively unreactive but can be attacked by electrophiles at ring nitrogen and certain carbon atoms. Pyridines undergo radical substitution reactions preferentially at the 2-position. Simple pyridines and their benzo derivatives are weak bases that form salts with strong acids. Various Lewis acids form complexes with pyridine and its benzo derivatives. The quaternization of pyridine and its benzo derivatives using alkyl and acyl halides have been used as versatile synthetic intermediates to biologically active compounds as final products. Precursors to cyanine dyes have been prepared by means of the 1,4-addition of pyridines and quinolines to acrylamide. N-oxides, obtained by the oxidation of pyridine and its benzo analogues, are versatile intermediates in organic synthesis.

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“…The 2-(trifluoromethyl)azaphenanthren-4-olsf were formed by a Conrad-Limpach-type condensation of the appropriate amine and ethyl trifluoroacetoacetate in polyphosphoric acid. 2-(Trifluoromethyl)benzo [Iz] quinolin-4-ol (1), 6-chloro-2-(trifluoromethyl)benzo [A]quinolin-4-ol (9), 6-cyano-2-(trifluoromethyl)benzo [h] quinolin-4-ol (10), 7nitro-2-(trifluoromethyl)benzo [h\quinolin-4-ol (11), 2-(trifluoromethyl)-l,7-phenanthrolin-4-ol (12), 2-(trifluoromethyl)-1,8-phenanthrolin-4-ol (13), 2-(trifluoromethyl)-1.10phenanthrolin-4-ol (14), 5-methoxy-2-(trifluoromethyl)-1.10phenanthrolin-4-ol (15), and 5-methyl-2-(trifluoromethyl)benzo [A]-1,6-naphthyridin-4-ol (16) were prepared from 1-naphthylamine, 4-chloro-1-naphthylamine, 4-amino-1-naphthalenecarbonitrile, 5-nitro-1-naphthylamine, 5-aminoisoquinoline, 8-aminoisoquinoline, 8-amino-6-methoxyquinoline, and 4-aminoquinaldine, respectively. The conversion of the 4-hydroxy compounds into the corresponding 4-bromo derivatives was accomplished with either phosphorus pentabromide, phosphorus oxybromide,8 phosphorus tribromide, or a mixture of phosphorus oxybromide and fThe 4-hydroxy derivatives of azaphenanthrenes exist in equilibrium with their keto tautomers which are believed to be the predominant form.7 For convenience, however, we refer to them simply as azaphenanthren-4-ols.…”

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confidence: 99%