M. V. Goryaeva, S. O. Kushch, Ya. V. Burgart, M. A. Ezhikova, M. I. Kodess, P. A. Slepukhin, A. A. Tumashov, L. L. Frolova, D. V. Sudarikov, V. I. Saloutin, “Monoterpene amino alcohols in multicomponent synthesis of chiral hetero- and carbocycles”, Mendeleev Commun., 2025, Volume 35, Issue 4,Pages <nobr>464

Communications

Monoterpene amino alcohols in multicomponent synthesis of chiral hetero- and carbocycles

M. V. Goryaeva^a, S. O. Kushch^a, Ya. V. Burgart^a, M. A. Ezhikova^a, M. I. Kodess^a, P. A. Slepukhin^a, A. A. Tumashov^a, L. L. Frolova^b, D. V. Sudarikov^b, V. I. Saloutin^a

^a I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 620108 Ekaterinburg, Russian Federation
^b Institute of Chemistry, Komi Science Center, Ural Branch of the Russian Academy of Sciences, 167000 Syktyvkar, Russian Federation

Abstract: The reaction between ethyl trifluoroacetoacetate, acetone and 4-amino-3-hydroxycarane having tertiary hydroxy group affords the 5-hydroxy-5-(trifluoromethyl)cyclohex-2-en-1-one derivative bearing 3-positioned (3-hydroxycaran-4-yl)amino moiety. The analogous reaction with 3-amino-2-hydroxyapopinane having functional groups at the secondary carbon atoms gives the product of further heterocyclization with perhydro 6,8-methanobenz[4,5]oxazolo[3,2-a]pyridine framework.

Keywords: monoterpenes, amino alcohols, β-pinene, 3-carene, ethyl trifluoroacetoacetate, acetone, multicomponent reactions, organofluorine compounds, cyclohex-2-en-1-one, 6,8-methanobenz[4,5]oxazolo[3,2-a]pyridine.

Received: 02.12.2024
Accepted: 05.02.2025

Language: English

DOI: 10.71267/mencom.7699

	*Supplementary materials:*
		Supplementary_data_1.pdf	2.9 Mb