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

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

Marina V Goryaeva 1
Marina V Goryaeva
Svetlana Olegovna Kushch 1
Svetlana Olegovna Kushch
Yanina Valer'evna Burgart 1
Yanina Valer'evna Burgart
Marina Aleksandrovna Ezhikova 1
Marina Aleksandrovna Ezhikova
Mikhail Isaakovich Kodess 1
Mikhail Isaakovich Kodess
Pavel Alexandrovich Slepukhin 1
Pavel Alexandrovich Slepukhin
Andrey Arturovich Tumashov 1
Andrey Arturovich Tumashov
Larisa Leonidovna Frolova 2
Larisa Leonidovna Frolova
Denis Vladimirovich Sudarikov 2
Denis Vladimirovich Sudarikov
Viktor Ivanovich Saloutin 1
Viktor Ivanovich Saloutin
1 I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 620108 Ekaterinburg, Russian Federation
2 Institute of Chemistry, Komi Science Center, Ural Branch of the Russian Academy of Sciences, 167000 Syktyvkar, Russian Federation
Published 2025-05-21
CommunicationVolume 35, Issue 4, 464-466
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Goryaeva M. V. et al. Monoterpene amino alcohols in multicomponent synthesis of chiral hetero- and carbocycles // Mendeleev Communications. 2025. Vol. 35. No. 4. pp. 464-466.
GOST all authors (up to 50) Copy
Goryaeva M. V., Kushch S. O., Burgart Y. V., Ezhikova M. A., Kodess M. I., Slepukhin P. A., Tumashov A. A., Frolova L. L., Sudarikov D. V., Saloutin V. I. Monoterpene amino alcohols in multicomponent synthesis of chiral hetero- and carbocycles // Mendeleev Communications. 2025. Vol. 35. No. 4. pp. 464-466.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.71267/mencom.7699
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7699
TI - Monoterpene amino alcohols in multicomponent synthesis of chiral hetero- and carbocycles
T2 - Mendeleev Communications
AU - Goryaeva, Marina V
AU - Kushch, Svetlana Olegovna
AU - Burgart, Yanina Valer'evna
AU - Ezhikova, Marina Aleksandrovna
AU - Kodess, Mikhail Isaakovich
AU - Slepukhin, Pavel Alexandrovich
AU - Tumashov, Andrey Arturovich
AU - Frolova, Larisa Leonidovna
AU - Sudarikov, Denis Vladimirovich
AU - Saloutin, Viktor Ivanovich
PY - 2025
DA - 2025/05/21
PB - Mendeleev Communications
SP - 464-466
IS - 4
VL - 35
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2025_Goryaeva,
author = {Marina V Goryaeva and Svetlana Olegovna Kushch and Yanina Valer'evna Burgart and Marina Aleksandrovna Ezhikova and Mikhail Isaakovich Kodess and Pavel Alexandrovich Slepukhin and Andrey Arturovich Tumashov and Larisa Leonidovna Frolova and Denis Vladimirovich Sudarikov and Viktor Ivanovich Saloutin},
title = {Monoterpene amino alcohols in multicomponent synthesis of chiral hetero- and carbocycles},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {May},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7699},
number = {4},
pages = {464--466},
doi = {10.71267/mencom.7699}
}
MLA
Cite this
MLA Copy
Goryaeva, Marina V., et al. “Monoterpene amino alcohols in multicomponent synthesis of chiral hetero- and carbocycles.” Mendeleev Communications, vol. 35, no. 4, May. 2025, pp. 464-466. https://mendcomm.colab.ws/publications/10.71267/mencom.7699.

Keywords

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

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.

Funders

Russian Science Foundation
24-13-00427

References

1.
Crystal structure refinement withSHELXL
Sheldrick G.M.
Acta crystallographica. Section C, Structural chemistry, 2015
2.
OLEX2: a complete structure solution, refinement and analysis program
Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A., Puschmann H.
Journal of Applied Crystallography, 2009
3.
SHELXT– Integrated space-group and crystal-structure determination
Sheldrick G.M.
Acta Crystallographica Section A: Foundations and Advances, 2015
4.
Synthesis of oxygen-containing heterocyclic compounds based on monoterpenoids
Patrusheva O.S., Volcho K.P., Salakhutdinov N.F.
Russian Chemical Reviews, 2018
5.
Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone
Banina O.A., Sudarikov D.V., Nigmatov A.G., Frolova L.L., Slepukhin P.A., Zlotin S.G., Kutchin A.V.
Russian Chemical Bulletin, 2017
6.
One-pot synthesis and antimicrobial evaluation of novel 3-cyanopyridine derivatives of (-)-β-pinene.
Liao S., Shang S., Shen M., Rao X., Si H., Song J., Song Z.
Bioorganic and Medicinal Chemistry Letters, 2016
7.
An overview of the pharmacological properties and potential applications of natural monoterpenes.
Koziol A., Stryjewska A., Librowski T., Salat K., Gawel M., Moniczewski A., Lochynski S.
Mini-Reviews in Medicinal Chemistry, 2014
8.
Therapeutic Potential of α- and β-Pinene: A Miracle Gift of Nature
Salehi B., Upadhyay S., Erdogan Orhan I., Kumar Jugran A., L.D. Jayaweera S., A. Dias D., Sharopov F., Taheri Y., Martins N., Baghalpour N., C. Cho W., Sharifi-Rad J.
Biomolecules, 2019
11.
Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications
Zielińska-Błajet M., Feder-Kubis J.
International Journal of Molecular Sciences, 2020
12.
Dual Stereoselectivity in the Dialkylzinc Reaction Using (−)-β-Pinene Derived Amino Alcohol Chiral Auxiliaries
Binder C.M., Bautista A., Zaidlewicz M., Krzemiński M.P., Oliver A., Singaram B.
Journal of Organic Chemistry, 2009
13.
Three-Component Synthesis of 7-Hydroxy-7-polyfluoroalkylhexahydroimidazo[1,2-a]­pyridin-5(1H)-ones
Goryaeva M.V., Burgart Y.V., Kudyakova Y.S., Ezhikova M.A., Kodess M.I., Slepukhin P.A., Saloutin V.I.
European Journal of Organic Chemistry, 2015
14.
Natural Monoterpenes: Much More than Only a Scent
Wojtunik‐Kulesza K.A., Kasprzak K., Oniszczuk T., Oniszczuk A.
Chemistry and Biodiversity, 2019
16.
Phytochemical composition, anti-inflammatory activity and cytotoxic effects of essential oils from three Pinus spp.
Basholli-Salihu M., Schuster R., Hajdari A., Mulla D., Viernstein H., Mustafa B., Mueller M.
Pharmaceutical Biology, 2017
17.
Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and alkyl amines: a novel approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones
Goryaeva M.V., Kushch S.O., Khudina O.G., Burgart Y.V., Kudyakova Y.S., Ezhikova M.A., Kodess M.I., Slepukhin P.A., Sadretdinova L.S., Evstigneeva N.P., Gerasimova N.A., Saloutin V.I.
Organic and Biomolecular Chemistry, 2019
19.
Zlotin S.G., Banina O.A., Sudarikov D.V., Nigmatov A.G., Frolova L.L., Kutchin A.V.
Mendeleev Communications, 2020
20.
Nitrogen-Containing Heterocyclic Compounds Obtained from Monoterpenes or Their Derivatives: Synthesis and Properties
Chernyshov V.V., Popadyuk I.I., Yarovaya O.I., Salakhutdinov N.F.
Topics in Current Chemistry, 2022
22.
Pyrazole derived from (+)-3-carene; a novel potent, selective scaffold for sphingosine-1-phosphate (S1P1) receptor agonists
Zécri F.J., Albert R., Landrum G., Hinterding K., Cooke N.G., Guerini D., Streiff M., Bruns C., Nuesslein-Hildesheim B.
Bioorganic and Medicinal Chemistry Letters, 2010
23.
Competitive ways for three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and amino alcohols
Saloutin V.I., Goryaeva M.V., Kushch S.O., Khudina O.G., Ezhikova M.A., Kodess M.I., Slepukhin P.A., Burgart Y.V.
Pure and Applied Chemistry, 2020
24.
New multicomponent approach to polyfluoroalkylated pyrido[1,2-a]pyrimidine derivatives and bis-cyclohexenones
Goryaeva M.V., Kushch S.O., Khudina O.G., Burgart Y.V., Ezhikova M.A., Kodess M.I., Slepukhin P.A., Volobueva A.S., Slita A.V., Esaulkova I.L., Misiurina M.A., Zarubaev V.V., Saloutin V.I.
Journal of Fluorine Chemistry, 2021
25.
Monoterpenes: Essential Oil Components with Valuable Features
Dehsheikh A.B., Sourestani M.M., Dehsheikh P.B., Mottaghipisheh J., Vitalini S., Iriti M.
Mini-Reviews in Medicinal Chemistry, 2020
30.
Li-Zhulanov N.S., Ponomarev K.Y., Sari S., Gülmez D., Arikan-Akdagli S., Krasnov V.I., Suslov E.V., Volcho K.P., Salakhutdinov N.F.
Mendeleev Communications, 2024