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Synthesis of some derivatives of alkaloids. VII

L. Dúbravková, I. Ježo, P. Šefčovič, and Z. Votický

Slovak Academy of Sciences, Bratislava

 

Abstract: cf. C.A. 50, 15551h. In order to get some insight into relation between the chem. structure of emetine and its physiol. action, the quinolizidine component of the mol. was studied. The following compds. were prepd.: β-methylglutarimide, b764 279-81°, m. 140-1°; α-ethylglutarimide, b756 279-81°, m. 89-91°; β-methyl-α-ethylglutarimide, b758 280-2°, m. 93-5°; γ-pipecoline, b756 132-4°; β-ethylpiperidine, b755 151-2°; 3-ethyl-4-methylpiperidine, b755 177-9°. The following 3,4,1-R3,R4(3,4-R1R2C6H3CH2CO)C5H8N (I) were reduced with LiAlH4 to the corresponding tertiary amine (II) (R1, R2, R3, R4, b.p./mm. for I and II, and m.p. of II.HCl given): H, H, H, H, 180-2°/9, 129-31°/9, 228-9°; (R1 + R2 =)CH2O2, H, H, 195-7°/0.3, 121-3°/0.4, 215-16°; MeO, MeO, H, H, 197-9°/0.3, 183-5°/9, 210-11°; H, H, H, Me, 182-3°/9, 130-1°/10, 260.5-1.5°; (R1 + R2 =)CH2O2, H, Me, 167-8°/0.03, 115-17°/0.06, 234-5°; MeO, MeO, H, Me, 186-8°/0.4, 135-7°/0.1. 204-5°; MeO, MeO, Et, H, 198-201°/0.5, 145-7°/0.2, 188-9°; MeO, MeO, Et, Me, 197-9°/0.1, 130-2°/0.01, 173-4°.

Full paper in Portable Document Format: 99a541.pdf (in Slovak)

 

Chemical Papers 9 (9) 541–546 (1955)

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