Heterocyclic Spiranes. Oxazolidines from (1-Aminocyclohexyl)methanol

(1-Aminocyclohexyl)methanol (I) has been condensed with five aldehydes and a ketone, cyclohexanone. The reaction with ketones appears limited largely to cyclic ketones. Heterocyclic spiro oxazolidines or their derivatives were obtained from condensations with formaldehyde (II), benzaldehyde (Ila-ilc), p-nitrobenzaldehyde (IIId, IIIe), and cyclohexanone (VIIa-VIIc), dispiro oxazolidines being formed in the latter case. Structures were established by comparison of infrared and ultraviolet or molecular refraction data with appropriate analogs in the literature. Phthalaldehydic acid yielded an amino acid (tentatively formulated as IV, in the solid state), which isomerizes to a lactone (IVa) in chloroform solution. Dehydration of IV with benzoyl chloride yielded an interesting heterocyclic spiro oxazolidine lactam (V). Cinnamaldehyde yielded the Schiff base, (1-cinnamalaminocyclohexyl)methanol (VI). Several other new derivatives of (1-aminocyclohexyl)methanol are described.