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Synthesis of 2-[2-isopropyl-4-(o-methoxyphenyl)-tetrahydropyran-4-yl]amine and its reaction with aromatic aldehydes

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Chemistry of Heterocyclic Compounds Aims and scope

A preparative method was developed for the synthesis of 2-isopropyltetrahydropyran-4-one, which was then transformed by the action of ethyl cyanoacetate into ethyl (2-isopropyl-4-tetrahydro-pyranylidene)cyanoacetate. Reaction of the latter with o-methoxyphenylmagnesium bromide followed by saponification and reduction with LiAlH4 led to 4-(2-aminoethyl)-2-isopropyl-4-(o-methoxy-phenyl)tetrahydropyran. A series of new azomethines, which are reduced to the corresponding amines by the action of NaBH4, were synthesized by the reaction of the above-mentioned amine with aromatic aldehydes.

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References

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Correspondence to G. A. Gevorgyan.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 838-842, June, 2010.

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Arutjunyan, N.S., Hakobyan, L.A., Hakobyan, N.Z. et al. Synthesis of 2-[2-isopropyl-4-(o-methoxyphenyl)-tetrahydropyran-4-yl]amine and its reaction with aromatic aldehydes. Chem Heterocycl Comp 46, 670–674 (2010). https://doi.org/10.1007/s10593-010-0567-1

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  • DOI: https://doi.org/10.1007/s10593-010-0567-1

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