Synthesis of Stable Atropisomers of Dialkyl-4-Ethoxy-1-(8-((2-ethoxy-2-oxoacetyl)-amino)-1-naphthyl)-5-oxo-4,5-dihydro-1H-pyrrole-2,3-dicarboxylates |
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Authors: | Issa Yavari Mehdi Adib Fatemeh Jahani-Moghaddam |
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Institution: | (1) Department of Chemistry, University of Tarbiat Modarres, Tehran, Iran, IR |
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Abstract: | Summary. Protonation of the reactive 1:1-intermediate produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates
with diethyl N,N′-(naphthalene-1,8-diyl)-dioxamate leads to a vinylphosphonium salt which undergoes an intramolecular Wittig reaction to produce dialkyl-4-ethoxy-1-(8-((2-ethoxy-2-oxoacetyl)-amino)-1-naphthyl)-5-oxo-4,5-dihydro-1H-pyrrole-2,3-dicarboxylates in good yields. The title compounds exist as stable rotamers as a result of restricted rotation
around the single bond linking the naphthalene moiety and the heterocyclic system. The calculated free energy of activation
for interconversion of the atropisomers amounts to about 102±2 kJ · mol−1.
Corresponding author. E-mail: isayavar@yahoo.com
Received February 5, 2002. Accepted March 19, 2002 |
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Keywords: | , ,Peri interaction, Hindered rotation, Stereochemistry, Rotational isomers, Intramolecular Wittig reaction, Triphenylphosphine, |
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