2007
DOI: 10.1007/s11172-007-0359-7
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Aroyl[bis(4-hydroxycoumarin-3-yl)]methanes in reactions with 1,2-diaminobenzenes

Abstract: The reaction of aroyl[bis(4 hydroxycoumarin 3 yl)]methanes with 1,2 phenylenediamines in Pr i OH is accompanied by the recyclization to 8 R or 7 R 4 (2 hydroxyphenyl) 1,5 benzodiazepin 2 ones, whereas the reaction with o phenylenediamine and its 4 methyl sub stituted derivatives in MeOH produces organic ionic salts of the bis coumarin anion with monoprotonated o phenylenediamine as the cation.Key words: aroyl[bis(4 hydroxycoumarin 3 yl)]methanes, 4 R 1,2 diaminobenzenes, 8 R (7 R) 4 (2 hydroxyphenyl) 1,5 benzo… Show more

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Cited by 16 publications
(14 citation statements)
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“…Results are given in Table 2 in which it is apparent that aryl glyoxals, including those bearing electron-poor and electron-rich substituents, were able to undergo this reaction. Compared with a previously reported method which has used AcOH as reaction media, 9 the present method provides environmentally safe conditions using water as solvent and p-TSA as catalyst to obtain the desired products with better yields than previous reported. Recently, organic synthesis on water has also been reviewed by Fokin and co-workers.…”
Section: Resultsmentioning
confidence: 80%
See 1 more Smart Citation
“…Results are given in Table 2 in which it is apparent that aryl glyoxals, including those bearing electron-poor and electron-rich substituents, were able to undergo this reaction. Compared with a previously reported method which has used AcOH as reaction media, 9 the present method provides environmentally safe conditions using water as solvent and p-TSA as catalyst to obtain the desired products with better yields than previous reported. Recently, organic synthesis on water has also been reviewed by Fokin and co-workers.…”
Section: Resultsmentioning
confidence: 80%
“…Traditionally, the most popular strategies towards the synthesis of dicoumarols start from salicylaldehyde and formaldehyde 6 and involve the biosynthesis of dicoumarol using micro-organisms such as Penicillium jenseni, 7 or require the Knoevenagel condensation of 4-hydroxycoumarins with carbonyl compounds using several catalysts. [8][9][10] For many years, chemical reactions in water have attracted the attention of chemists. 11 From an environmental and economic point of view, water as a solvent or media has many advantages and usually results in excellent efficiency and selectivity.…”
Section: Introductionmentioning
confidence: 99%
“…Literature survey shows that these bis-adducts based on heterocyclic CH acids and active carbonyl compounds have attracted interest in organic synthesis. 13 A plausible mechanism for this reaction is proposed in Scheme 2. As reported in the literature, first nuleophilic addition of 4-hydroxycoumarin to polar carbonyl bond of aldehydes gives I, followed by loss of H 2 O to afford II.…”
Section: Resultsmentioning
confidence: 99%
“…Products were characterized by comparison of spectroscopic data (IR, 1 H NMR, 13 C NMR spectra) and melting points with authentic samples. The NMR spectra were recorded on a Bruker Avance DPX 300 MHz instrument.…”
Section: Methodsmentioning
confidence: 99%
“…It is noteworthy to mention that these ZnO-catalyzed reactions showed the chemoselectivity toward pyranocoumarins 4 instead of biscoumarins 5 which was reported in the previous literature. 21 To determine suitable conditions, the preparation of 4a was selected as a model. In the first attempt, compound 4a was not produced in absence of catalyst even after 180 min.…”
Section: Figurementioning
confidence: 99%