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Azomethine ylides derived from dichlorocarbene and O-acylsalicylaldehyde anils in the synthesis of 2,5-epoxy-2,3,4,5-tetrahydro-1,4-benzoxazepin-2-ones and 2-aminoethanols

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Abstract

Iminiodichloromethanides generated by the reaction of O-acylsalicylaldehyde anils with dichlorocarbene undergo regioselective intramolecular 1,3-dipolar cycloaddition to the ester carbonyl group to give 2,5-epoxy-2,3,4,5-tetrahydro-1,4-benzoxazepin-2-ones. These compounds are expedient precursors for the synthesis of N-(2-hydroxybenzyl)ethanolamines.

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Authors and Affiliations

  1. Department of Chemistry, St.-Petersburg State University, 26 Universitetsky prosp., 198504, St.-Petersburg, Russian Federation

    I. V. Voznyi, M. S. Novikov, A. F. Khlebnikov & R. R. Kostikov

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  1. I. V. Voznyi
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  2. M. S. Novikov
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  3. A. F. Khlebnikov
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  4. R. R. Kostikov
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Voznyi, I.V., Novikov, M.S., Khlebnikov, A.F. et al. Azomethine ylides derived from dichlorocarbene and O-acylsalicylaldehyde anils in the synthesis of 2,5-epoxy-2,3,4,5-tetrahydro-1,4-benzoxazepin-2-ones and 2-aminoethanols. Russian Chemical Bulletin 53, 1087–1091 (2004). https://doi.org/10.1023/B:RUCB.0000041304.68814.83

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  • DOI: https://doi.org/10.1023/B:RUCB.0000041304.68814.83

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