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Synthesis of 6-(α-thienyl)azulene from 2-butoxy-4-(α-thienyl)-Δ5-dihydropyran

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2,5-Dibutoxy-4-(α-thienyl)-Δ3-dihydropyran was obtained by bromoalkoxylation at the double bond and dehydrobromination of 2-butoxy-4-(α-thienyl)-Δ5-dihydropyran. Acid hydrolysis of the product in the presence of N-methylaniline hydrochloride gave a salt of 3-(α-thienyl)glutaconic dialdehyde dianil, treatment of which with cyclopentadienylsodium in alcohol gives the corresponding fulvene, which is thermally cleaved to N-methylaniline and 6-(α-thienyl)azulene.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1329–1331, October, 1974.

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Porshnev, Y.P., Tereshchenko, E.M. & Mochalin, V.B. Synthesis of 6-(α-thienyl)azulene from 2-butoxy-4-(α-thienyl)-Δ5-dihydropyran. Chem Heterocycl Compd 10, 1156–1158 (1974). https://doi.org/10.1007/BF00470153

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  • DOI: https://doi.org/10.1007/BF00470153

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