Novel Synthesis of 2‐Oxo‐2H‐Benzopyrano[2,3‐d]Pyrimidines

Turki, H.; Abid, Souhir; Bigot, Y. Le; Fery–Forgues, Suzanne; Gharbi, Rachid El

doi:10.1081/scc-200031013

Cited by 28 publications

(13 citation statements)

References 6 publications

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“…Iminocoumarin 1 was obtained by Knoevenagel condensation followed by N-ethoxycarbonylation as previously described in [9]. The condensation of this compound with various hydrazides (2-11, see Table 1) was studied, first focusing on a specific system, namely 1 and benzoic hydrazide 2 (Scheme 1), to determine the best conditions for synthesis.…”

Section: Resultsmentioning

confidence: 99%

“…All spectrophotometric measurements were conducted in a thermostated cell at 25 C. 3-Cyano-N-ethoxycarbonyl-7-diethylamino iminocoumarin 1. 3-Cyano-N-ethoxycarbonyl-7-diethylamino iminocoumarin 1 was prepared as previously described in [9].…”

Section: Methodsmentioning

confidence: 99%

“…Different routes have been described in the literature for the synthesis of this class of condensed heterocycles [6][7][8]. As part of our investigations on the synthesis of benzopyranopyrimidines, we have reported previously [9], a new method based on the transformation of 3-cyano-iminocoumarins under the action of primary aliphatic and aromatic amines, on heating in methanol. We have shown that the reaction proceeded by an original mechanism that involves several consecutive steps including nucleophilic attack of the iminolactone ring, pyran ring opening, E/Z isomerization, and subsequent cyclization.…”

Section: Introductionmentioning

confidence: 99%

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Reactivity of 3‐cyano‐N‐ethoxycarbonyl‐iminocoumarin with hydrazides as N‐nucleophiles

Kammoun¹,

Turki²,

Gharbi³

et al. 2009

Journal of Heterocyclic Chem

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Condensation of 3‐cyano‐7‐diethylamino‐N‐ethoxycarbonyl‐iminocoumarin with various hydrazides as N‐nucleophiles gave a new series of 2‐oxo‐2H‐1‐benzopyrano[2,3‐d]pyrimidines bearing an acylhydrazino fragment in the 4‐position. The structures of the products obtained were characterized using IR, 1H NMR, 13C NMR and elemental analysis. The optical properties were reported for three of these compounds. J. Heterocyclic Chem., (2009).

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Reactivity of 3‐cyano‐N‐ethoxycarbonyl‐iminocoumarin with hydrazides as N‐nucleophiles

Kammoun¹,

Turki²,

Gharbi³

et al. 2009

Journal of Heterocyclic Chem

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“…Ultrapure water with a resistivity of 16 MΩ cm was produced using a Milli-Q apparatus (Millipore). Dyes 1-3 were synthesized as previously described [15]. Dye 1 resulted from the condensation of o-hydroxybenzaldehyde with an equimolecular amount of malononitrile in the presence of piperidine as the catalyst, and was recrystallised in ethanol.…”

Section: Methodsmentioning

confidence: 99%

“…However, it seems possible to us that the behaviour observed is linked to the presence of the benzimidazolyl fragment, because immobilization of the latter by subsequent reaction leads to highly fluorescent dyes [13,14]. In our team, we recently reported the synthesis of 10 new iminocoumarins that bear a cyano group as an electronwithdrawing moiety at the 3-position [15]. A preliminary spectroscopic study was carried out in dichloromethane [16].…”

Section: Introductionmentioning

confidence: 96%

Optical properties of new fluorescent iminocoumarins. Part 2. Solvatochromic study and comparison with the corresponding coumarin

Turki

Abid

Gharbi

et al. 2006

Comptes Rendus Chimie

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Tracking Chemical Kinetics in High‐Throughput Systems

Boelens

Iron

Westerhuis

et al. 2003

Chemistry A European J

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Combinatorial chemistry and high-throughput experimentation (HTE) have revolutionized the pharmaceutical industry-but can chemists truly repeat this success in the fields of catalysis and materials science? We propose to bridge the traditional "discovery" and "optimization" stages in HTE by enabling parallel kinetic analysis of an array of chemical reactions. We present here the theoretical basis to extract concentration profiles from reaction arrays and derive the optimal criteria to follow (pseudo)first-order reactions in time in parallel systems. We use the information vector f and introduce in this context the information gain ratio, chi(r), to quantify the amount of useful information that can be obtained by measuring the extent of a specified reaction r in the array at any given time. Our method is general and independent of the analysis technique, but it is more effective if the analysis is performed on-line. The feasibility of this new approach is demonstrated in the fast kinetic analysis of the carbon-sulfur coupling between 3-chlorophenylhydrazonopropane dinitrile and beta-mercaptoethanol. The theory agrees well with the results obtained from 31 repeated C-S coupling experiments.

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Novel Synthesis of 2‐Oxo‐2H‐Benzopyrano[2,3‐d]Pyrimidines

Cited by 28 publications

References 6 publications

Reactivity of 3‐cyano‐N‐ethoxycarbonyl‐iminocoumarin with hydrazides as N‐nucleophiles

Reactivity of 3‐cyano‐N‐ethoxycarbonyl‐iminocoumarin with hydrazides as N‐nucleophiles

Optical properties of new fluorescent iminocoumarins. Part 2. Solvatochromic study and comparison with the corresponding coumarin

Tracking Chemical Kinetics in High‐Throughput Systems

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