The Degradation of a Derivative of Benzyl Styryl Ketone to trans-Cinnamic Acid<sup>1</sup>

Sapper, David I.; Southwick, Philip L.

doi:10.1021/jo01107a022

Cited by 4 publications

(2 citation statements)

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“…Under the reaction conditions (110 °C), 2-aminopyridine becomes a liquid and dissolves all components of the reaction sufficiently. These data are in good agreement with the data obtained in kinetic and other studies − of the Ortoleva–King reaction.…”

Section: Resultssupporting

confidence: 91%

“…First Ortoleva, and then King, demonstrated that pyridinium salts can often be conveniently prepared in a direct synthesis by heating active methyl and methylene compounds with iodine in pyridine. The yields of this elegant method are usually very good, and a variety of heterocyclic bases may be used instead of pyridine, including quinolines, isoquinolines, picolines, and nicotinamide . The reaction has been extended to include a variety other compounds containing active methyl and methylene groups.…”

Section: Resultsmentioning

confidence: 99%

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Imidazo[1,2-a]pyridines Susceptible to Excited State Intramolecular Proton Transfer: One-Pot Synthesis via an Ortoleva–King Reaction

et al. 2012

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A short and efficient route to a broad range of imidazo[1,2-a]pyridines from 2-aminopyridines and acetophenones is achieved by a tandem, one-pot process starting with an Ortoleva-King reaction. Optimal conditions for the first step were established after examining various reaction parameters (solvent, reagent ratios, and temperature). The conditions identified (1st step, neat, 2.3 equiv of 2-aminopyridine, 1.20 equiv of I(2), 4 h, 110 °C; 2nd step, NaOH(aq), 1 h, 100 °C) resulted in the formation of imidazo[1,2-a]pyridines in 40-60% yields. The synthesis is compatible with various functionalities (OH, NMe(2), Br, OMe). Products containing a 2-(2'-hydroxyphenyl) substituent undergo excited state intramolecular proton transfer (ESIPT) in nonpolar and polar-aprotic solvents. Although ESIPT-type emission in nonpolar solvents is weak, the Stokes shifts are very high (11000 cm(-1)). The comparison of the properties of six ESIPT-capable imidazo[1,2-a]pyridines shows the influence of various substituents on emission characteristics. All of them also display strong, solid-state emission in blue-green-yellow region. 2-Aryl-imidazo[1,2-a]pyridines not capable of ESIPT emit in the blue region, displaying high fluorescence quantum yield.

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