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New method for the synthesis of macrocyclic compounds

XIV. Intramolecular acylation of acid chlorides of ω-[3-(or 4)methyl-2-thienyl]alkanoic acids. Synthesis of muscone

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The intramolecular acylation of acid chlorides of ω-(3-methyl-2-thienyl)- and ω-(4-methyl-2-thienyl)alkanoic acids proceeds at the free 5 position of the thiophene ring. A solid-phase effect (silica gel), which, under comparable conditions, leads to more than double the yields, is displayed during the cyclization of acid chlorides of the above acids. A modification was developed for the reductive desulfurization of cyclothienones with alkyl groups in the β position of the thiophene ring; the modification includes the formation of unsaturated compounds and products of the reduction of the carbonyl group. A new route to the synthesis of γ- and β-methylcycloalkanones, including DL-muscone, was developed.

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See [2] for communication XIII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 170–176, February, 1972.

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Taits, S.Z., Kalinovskii, O.A., Bogdanov, V.S. et al. New method for the synthesis of macrocyclic compounds. Chem Heterocycl Compd 8, 149–155 (1972). https://doi.org/10.1007/BF00472345

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  • DOI: https://doi.org/10.1007/BF00472345

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