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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| Authors: | Géza Stájer Angela E Szabó Ferenc Fülöp Gábor Bernáth Pál Sohár |
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| Institution: | 1. Institute of Pharmaceutical Chemistry, University Medical School Szeged, PO 121, H-6701 Szeged, Hungary;2. EGYT Pharmacochemical Works, POB 100, H-1475 Budapest, Hungary |
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| Abstract: | 3-exo-Aminobicyclo2.2.1]hept-5-ene-2-exo-carboxylic acid and ethyl 3-endo-aminobicyclo2.2.1]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. |
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