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Stereodirected reactions of salicilaldehyde derivatives with tert-butyl 3(4)-hydroxy-2(3)-(3-methylbut-2-enyl)- piperidine-1-carboxylates as an efficient preparation procedure of tetrahydropyran derivatives fused with a piperidine ring

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Abstract

Reaction of salicilaldehyde and its derivatives with unsaturated cis-, trans-alcohols of the piperidine series in the presence of methyl orthoformate and p-toluenesulfonic acid led to the formation of a new heterocyclic system connecting four fuzed rings (two tetrahydropyrans, a piperidine, and an aromatic ring), 6,6-dimethyl-6а,7,7а,8(9),10,11,11а,12а-octahydrochromeno[3′,4′:5,6]pyranо[3,2-с(b)]pyridine.

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Authors and Affiliations

  1. Timiryazev Russian State Agrarian University (MSKhA), ul. Timiryazeva 49, Moscow, 127550, Russia

    V. I. Boev & S. L. Belopukhov

  2. Lipetsk State Pedagogical University, Lipetsk, Russia

    A. I. Moskalenko & G. N. Nikonova

Authors
  1. V. I. Boev
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  2. A. I. Moskalenko
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  3. S. L. Belopukhov
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  4. G. N. Nikonova
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Correspondence to V. I. Boev.

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Original Russian Text © V.I. Boev, A.I. Moskalenko, S.L. Belopukhov, G.N. Nikonova, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 8, pp. 1162–1169.

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Boev, V.I., Moskalenko, A.I., Belopukhov, S.L. et al. Stereodirected reactions of salicilaldehyde derivatives with tert-butyl 3(4)-hydroxy-2(3)-(3-methylbut-2-enyl)- piperidine-1-carboxylates as an efficient preparation procedure of tetrahydropyran derivatives fused with a piperidine ring. Russ J Org Chem 52, 1154–1161 (2016). https://doi.org/10.1134/S1070428016080108

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  • DOI: https://doi.org/10.1134/S1070428016080108

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