Heterocyclic Spiranes. Oxazolidines from (1-Aminocyclohexyl)methanol

Wayland E Noland, Roy A. Johnson

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

(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.

Original languageEnglish (US)
Pages (from-to)1155-1159
Number of pages5
JournalJournal of Organic Chemistry
Volume25
Issue number7
DOIs
StatePublished - Jan 1 1960

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Ketones
Methanol
Derivatives
Lactams
Schiff Bases
Lactones
Chloroform
Refraction
Dehydration
Aldehydes
Formaldehyde
Condensation
Infrared radiation
Amino Acids
Acids
oxazolidine
spiro-oxazolidine
cyclohexanone

Cite this

Heterocyclic Spiranes. Oxazolidines from (1-Aminocyclohexyl)methanol. / Noland, Wayland E; Johnson, Roy A.

In: Journal of Organic Chemistry, Vol. 25, No. 7, 01.01.1960, p. 1155-1159.

Research output: Contribution to journalArticle

Noland, Wayland E ; Johnson, Roy A. / Heterocyclic Spiranes. Oxazolidines from (1-Aminocyclohexyl)methanol. In: Journal of Organic Chemistry. 1960 ; Vol. 25, No. 7. pp. 1155-1159.
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N2 - (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.

AB - (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.

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