Greenwood D T, Mallion K B, Todd A H, Turner R W
J Med Chem. 1975 Jun;18(6):573-7. doi: 10.1021/jm00240a009.
Some 2-aryloxymethyl-2,3,5,6-tetrahydro-1,4-oxazines have been shown to possess marked antidepressant activity. The 1,4-oxazines were synthesized by lithium aluminum hydride reduction of the readily available 6-aryloxymethyl-2,3,5,6-tetrahydro-1,4-oxazin-3-ones. High antidepressant activity was associated with ortho substitution of the 2-phenoxymethyl group and with 1,4-oxazines devoid of 4-substituents.