1999
DOI: 10.1021/ol990975s
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Novel Cyclic Molecules:  Selective Synthesis of Cyclic Phenylazomethines

Abstract: Novel cyclic molecules, the cyclic phenylazomethine trimers (CPAs), were synthesized via the dehydration of the 4-aminobenzophenone derivatives. The yields of the CPAs were enhanced to over 90% by induction of the bulky r-substituent to the substrate. The UV−vis spectra of the CPAs show a nonconjugated structure and Z conformation compared to the linear oligophenylazomethines (OPAs).

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Cited by 55 publications
(22 citation statements)
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“…pharmaceuticals, or rubber additives [1] and as amino protective groups in organic synthesis [2][3][4][5]. They also have uses as liquid crystals, [6] and in analytical, [7] medicinal [8] and polymer chemistry [9]. Conventionally Schiff bases have been prepared by refluxing mixtures of the amine and the carbonyl compound in an organic solvent, for example, ethanol or methanol [10], but variations are known, such as treatment of the same mixture at room temperature, refluxing the mixture in heptane in the presence of acetic acid [12], or azeotroping the mixture with benzene in a Dean-Stark apparatus in the presence of acid [13].…”
Section: Introductionmentioning
confidence: 99%
“…pharmaceuticals, or rubber additives [1] and as amino protective groups in organic synthesis [2][3][4][5]. They also have uses as liquid crystals, [6] and in analytical, [7] medicinal [8] and polymer chemistry [9]. Conventionally Schiff bases have been prepared by refluxing mixtures of the amine and the carbonyl compound in an organic solvent, for example, ethanol or methanol [10], but variations are known, such as treatment of the same mixture at room temperature, refluxing the mixture in heptane in the presence of acetic acid [12], or azeotroping the mixture with benzene in a Dean-Stark apparatus in the presence of acid [13].…”
Section: Introductionmentioning
confidence: 99%
“…Thermal stability of polyketanils with naphthalene pendant groups was studied by Sęk [22]. Linear and cyclic oligomers from 4-aminobenzophenone and dendritic oligomers were synthesized by Yamamoto et al [23][24][25][26][27][28][29]. Our previous paper [30] reported the synthesis and properties of some aliphatic polyketanils.…”
Section: Introductionmentioning
confidence: 99%
“…Imines are widely applied as analitycal, medicinal, polymer and liquid crystalline materials, [1][2][3] and as synthons in organic synthesis. 4,5 Conjugation of the triple bond and imino group in 1,3-aza-enynes provides further synthetic possibilities.…”
Section: Introductionmentioning
confidence: 99%