Stereochemical studies. 81. Saturated heterocycles. 69 . Preparation of methylene‐bridged 3,1‐benzoxazines, 3,1‐benzoxazin‐2‐ones and 3,1‐benzoxazine‐2‐thiones

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Abstract

3‐exo‐Aminobicyclo[2.2.1]hept‐5‐ene‐2‐exo‐carboxylic acid and ethyl 3‐endo‐aminobicyclo[2.2.1]heptane‐2‐endo‐carboxylate (6) were reduced with lithium aluminum hydride to the corresponding bicyclic aminoalcohols 3 and 4. These and the saturated endo‐endo and exo‐exo N‐methylaminoalcohols 16 and 22, respectively, were converted to methylene‐bridged tetrahydro‐ (11) and hexahydro‐3,1‐benzoxazin‐2‐ones 12, 17, 23 and 3,1‐benzoxazin‐2‐thiones 13, 14, 18, 24. The exo‐exo 3 and endo‐endo 4 aminoalcohols were cyclized by means of ethyl arylimidates to tricyclic dihydro‐1,3‐oxazines 7a‐d, 8a‐d. The structures were confirmed by ir, 1H and 13C nmr spectroscopy.

Original languageEnglish
Pages (from-to)1373-1376
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume21
Issue number5
DOIs
Publication statusPublished - Jan 1 1984

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ASJC Scopus subject areas

  • Organic Chemistry

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