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Title
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Synthesis of dimethyl 1-aryl-4- ethoxy-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylates mediated by triphenylphosphine
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Type
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JournalPaper
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Keywords
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Hindered rotation; Intramolecular Wittig reaction; Atropisomers; Acetylenic esters; Triphenylphosphine.
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Abstract
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Ethyl 2-arylamino-2-oxo-acetates undergo a complex reaction with dimethyl acetylendicarboxylate in the presence of triphenylphosphine to produce dimethyl l-aryl-4-ethoxy-5-oxo-4,5-dihydro-1H-pyrrole-2,3-dicarboxylates in good yields. Dynamic NMR study of dimethyl 1-(2-methyl-6-nitrophenyl)-4-ethoxy-5-oxo-4,5-dihydro-1H-pyrrole-2,3-dicarboxylate shows a fairly high energy barrier (∆G≠ = 95 ± 2 kJ mol-1) for rotation around the N-aryl single bond, which leads to an observable atropisomerism.
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Researchers
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Hoorieh Djahaniani (Third Researcher), Farough Nasiri (Second Researcher), yavari Issa (First Researcher)
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