Synthesis 1990; 1990(2): 153-156
DOI: 10.1055/s-1990-26819
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Regioselective Reductive Ring Cleavage of 3-Benzyltetrahydro-1,3-oxazines to 3-Dialkylaminopropanols and of 3-Benzyl-3-methyltetrahydro-1,3-oxazinium Iodides to Alkyl 3-Dialkylaminopropyl Ethers

Angel Alberola* , M. Angeles Alvarez, Celia Andrés, Alfonso González, Rafael Pedrosa
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, E-47011 Valladolid, Spain
Further Information

Publication History

Publication Date:
17 September 2002 (online)

3-Benzyltetrahydro-1,3-oxazines and their methiodides are ring-cleaved upon reduction with lithium aluminum hydride to give 3-dialkylaminopropanols or alkyl 3-dialkylaminopropyl ethers, respectively, in good yields. The reducing agent regioselectively cleaves the C-O bond in tetrahydro-1,3-oxazines and the C-N bond in the tetrahydro-1,3-oxazinium salts.

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