Abstract
Catalytic [6π + 2π]-cycloaddition of N-carbocholesteroxyazepine with functionally substituted terminal alkynes and 1,4-butynediol was performed for the first time under the action of the Co(acac)2(dppe)/Zn/ZnI2 three-component catalytic system. The reaction gave previously undescribed but promising 9-azabicyclo[4.2.1]nona-2,4,7-trienes (in 79–95% yields), covalently bound to a natural metabolite, cholesterol. The structure of the synthesized azabicycles was confirmed by analysis of one- and two-dimensional (1H, 13C, DEPT 13C, COSY, NOESY, HSQC, HMBC) NMR spectra.
Funder
Russian Science Foundation
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Cited by
6 articles.
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1. Cobalt(I)-catalyzed [6π+2π]-cycloaddition of 1,3-diynes to cyclohepta-1,3,5-triene in the synthesis of new disubstituted bicyclo[4.2.1]nona-2,4,7-trienes;Russian Chemical Bulletin;2023-10
2. Recent progress in applications of cobalt catalysts in organic reactions;Tetrahedron;2023-04
3. Synthesis of New Fluorene-Containing 9-Azabicyclo[4.2.1]nona-2,4,7-trienes by [6π+2π]-Cycloaddition of Alkynes to 9H-Fluoren-9-ylmethyl 1H-Azepine-1-carboxylate;Russian Journal of Organic Chemistry;2022-12
4. Co(I)-Catalyzed [4π + 2π] Cycloaddition of 1,2-Dienes to 1,3,5-Cyclooctatriene in the Synthesis of Previously Undescribed Tricyclo[4.2.2.02,5]Decenes;ECSOC-25;2021-11-12
5. Synthesis of New Functionally Substituted Bicyclo[4.2.1]nona-2,4,7-trienes by Co(I)-Catalyzed [6π + 2π] Cycloaddition of 1-Benzoylcycloheptatriene;ECSOC-25;2021-11-12