Structure, reactivity, and application of some triketone derivatives

Chen, Yousheng; Kuo, Ping‐Chang; Shie, Tien-Lan; Yang, Ding‐Yah

doi:10.1016/j.tet.2006.07.053

Cited by 46 publications

(31 citation statements)

References 13 publications

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“…Pyridylcoumarins 4, similar to previously studied derivatives of 4-hydroxycoumarin [16][17][18], may exist in theory in several tautomeric forms. The two most likely forms are shown below.…”

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confidence: 82%

Synthesis and structure of 4-hydroxy-3-pyridylcoumarins

Manaev

Voevodina

Traven

2009

Chem Heterocycl Comp

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confidence: 82%

Synthesis and structure of 4-hydroxy-3-pyridylcoumarins

Manaev

Voevodina

Traven

2009

Chem Heterocycl Comp

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“…This repulsion can be easily relieved via enolization of the 3-acyl group of 6, followed by a 1,5-acyl transfer reaction to afford enol acetate 10. The resulting 11 can then undergo esterification again to obtain enol diacetate 11 (Chen et al, 2006) (Scheme 7).…”

Section: Acetylation Reactionmentioning

confidence: 99%

3-Acetyl-4-hydroxycoumarin: Synthesis, reactions and applications

Abdou

2017

Arabian Journal of Chemistry

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The chemistry of 3-acetyl-4-hydroxycoumarin has gained increased interest in both synthetic organic and biological fields, since a large number of developments in the use of such compound seem to be of considerable value. This review summarizes results from the literature concerning the synthesis and reactions of 3-acetyl-4-hydroxycoumarin as well as its applications are also discussed.ª 2014 Production and hosting by Elsevier B.V. on behalf of King Saud University.

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“…Given that most reported acidichromic colorants contain only one pH-sensitive functional group in their molecules, their color changes are limited to a narrow pH range. In an effort to develop acidichromic colorants that can change their color under both extremely high basicity and high acidity, we have previously reported [12][13] the rational design and chemical synthesis of a novel acidichromic colorant 1 by the combination of an acid and base-sensitive triketone-containing functional group with an anilinecontaining molecule. The resulting compound underwent two distinct and reversible color changes under strong acidic and basic conditions (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of a Coumarin-based Acidichromic Colorant

2007

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This paper describes the fine-tuning of the acidichromic properties of a coumarin-containing colorant 1 by incorporation of electron-donating and electronwithdrawing substituents on the coumarin moiety. Colorant 1 can undergo two distinct and reversible color changes under both strongly acidic and basic conditions, but not in the presence of gaseous ammonia. The results indicated that the bromo-substituted compound 5b changes from red to yellow when exposed to gaseous ammonia, both in solution and on polycarbonate film, suggesting that an electron-withdrawing group at the 7-position of the coumarin moiety made the enolic hydrogen on 5b more susceptible to deprotonation by a base than in the unsubstituted compound 1.

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Structure, reactivity, and application of some triketone derivatives

Cited by 46 publications

References 13 publications

Synthesis and structure of 4-hydroxy-3-pyridylcoumarins

Synthesis and structure of 4-hydroxy-3-pyridylcoumarins

3-Acetyl-4-hydroxycoumarin: Synthesis, reactions and applications

Design and Synthesis of a Coumarin-based Acidichromic Colorant

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