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

Stájer Géza | Zendy; Szabó Angela E. | Zendy; Fülöp Ferenc | Zendy; Bernáth Gábor | Zendy; Sohár Pál | Zendy

Premium

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

Author(s) -

Stájer Géza,

Szabó Angela E.,

Fülöp Ferenc,

Bernáth Gábor,

Sohár Pál

Publication year - 1984

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570210526

Subject(s) - chemistry , bicyclic molecule , heptane , methylene , aluminum hydride , tricyclic , lithium aluminium hydride , lithium (medication) , nuclear magnetic resonance spectroscopy , stereochemistry , medicinal chemistry , organic chemistry , ion , methoxide , medicine , endocrinology

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, 1 H and 13 C nmr spectroscopy.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research