Halogenation of 2-Hydroxynicotinic Acid

Gero, Thomas W.; Jaques, Larry W.; Mays, Richard P.; Reid, D. H.; Shamblee, D. A.; Lo, Young S.

doi:10.1080/00397918908050699

Cited by 9 publications

(3 citation statements)

References 5 publications

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“…Substitution of the 2‐hydroxy group in pyridine compound 5 by reaction with thionyl chloride afforded the corresponding 2‐chloro derivative 6 5b,5c. Next, compound 6 was heated with benzylamine or butylamine to provide the corresponding 2‐aminopyridine derivatives 4b and 4c .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Pyridodiazepinediones by Using the Ugi Multicomponent Reaction

et al. 2010

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Benzodiazepines show a broad spectrum of biological activities. In an ongoing effort to extend molecular diversity in this type of systems, we developed a strategy for synthesizing3,4‐dihydro‐1H‐pyrido[2,3‐e][1,4]diazepine‐2,5‐dione compounds starting from 2‐hydroxynicotinic acid and by using an Ugi reaction as a key step in the synthesis. We opted to use 2‐isocyanophenyl benzoate instead of Armstrong's convertible isocyanide in this multicomponent reaction.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Pyridodiazepinediones by Using the Ugi Multicomponent Reaction

et al. 2010

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“…3-Carboxy-5-chloro-2-pyridone (4h) was prepared by adding dropwise a 20 wt % solution of t -BuOK in THF (26.3 mmol, 1.05 equiv) to a suspension of dimethyl malonate (25 mmol) in dry THF (50 mL) at 0 °C. The reaction mixture was stirred at room temperature for 45 min, and the vinamidinium hexafluorophosphate salt (37.5 mmol, 1.5 equiv) was added in one portion.…”

Section: Methodsmentioning

confidence: 99%

A General Preparation of Pyridines and Pyridones via the Annulation of Ketones and Esters

Marcoux

Marcotte

et al. 2001

J. Org. Chem.

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A general preparation of pyridines 4a-f from stabilized ketones 3a-c and aryl ketones 3d-f is described. The annulation of stabilized esters 3g,h gives access to the corresponding 2-pyridones 4g,h. The annulation reactions proceed in fair to excellent yields (46-87%) with vinamidinium hexafluorophosphate salts 2a-d containing electron-withdrawing groups at the beta-position. The mechanism of the reaction was investigated by NMR and proceeds through the formation of a dienaminone intermediate.

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“…1). Commercially available 2-hydroxynicotinic acid 1 was converted to dihalonicotinic acid 3 via two sequential halogenation reactions (Van den Bogaert et al, 2010;Gero et al, 1989;Haché et al, 2002), after which a benzylamine substituent was introduced yielding the aza-anthranilic acid derivative 4. Next, ester compound 5 was prepared from intermediate 4 and tert-butyl glycinate using a standard coupling procedure.…”

Section: Chemical Contextmentioning

confidence: 99%