Synthesis and structure of 1-(buta-1,3-dien-2-yl)pyrazoles and their behavior in Diels-Alder reactions |
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Authors: | O S Attaryan A O Baltayan G A Panosyan S A Sargsyan S G Matsoyan |
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Institution: | (1) Institute of Organic Chemistry, National Academy of Sciences of Armenia, ul. Zakariya Sarkavaga 167a, Erevan, 375091, Armenia;(2) Molecular Structure Research Center, National Academy of Sciences of Armenia, Erevan, Armeniya |
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Abstract: | A convenient procedure has been developed for the synthesis of cis-and trans-isomeric 1-(buta-1,3-dien-1-yl)-1H-pyrazoles by reaction of the corresponding pyrazoles with β-methylacrolein diethyl acetal and subsequent 1,4-cleavage of the nucleophilic substitution products. The behavior of the title compounds in Diels-Alder reactions with maleic anhydride has been studied. According to the 1H NMR data, 1-(buta-1,3-dien-1-yl)-1H-pyrazole is a mixture of cis and trans isomers. Butadienylpyrazoles having methyl groups in the pyrazole ring do not react with maleic anhydride. |
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