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Cyclic Sulfites, Key Intermediates in Synthesis of 1-Alkylamino-3-aryloxy-2-propanols from Glycidol

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Abstract

By treating glycidol with phenols a number of 3-aryloxypropanedioles were obtained. The latter with thionyl chloride afforded 4-aryloxymethyl-1,3,2-dioxathiolane 2-oxides. These compounds were also obtained from 4-chloromethyl-1,3,2-dioxathiolane 2-oxides by substitution aryloxy group for chlorine. The cyclic sulfides synthesized are universal intermediates in the synthesis of chiral aryloxypropanolamines among which are known β-adrenoblockaders, cardiovascular drugs. From (S)-glycidol were synthesized (S)-alprenolol, (S)-propanolol, and (S)-thymolol.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, 420088, Russia

    Z. A. Bredikhina, D. V. Savel'ev & A. A. Bredikhin

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  1. Z. A. Bredikhina
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  2. D. V. Savel'ev
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  3. A. A. Bredikhin
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Bredikhina, Z.A., Savel'ev, D.V. & Bredikhin, A.A. Cyclic Sulfites, Key Intermediates in Synthesis of 1-Alkylamino-3-aryloxy-2-propanols from Glycidol. Russian Journal of Organic Chemistry 38, 213–219 (2002). https://doi.org/10.1023/A:1015561532507

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