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DOI: 10.1055/s-0040-1706005
Diversity-Oriented Synthesis of Novel Trihalomethyl-Containing Spirochromeno[3,4-a](thia)pyrrolizidines and Spirochromeno-[3,4-a]indolizidines by One-Pot, Three-Component [3+2]-Cycloaddition Reaction
The work was financially supported by the Russian Foundation for Basic Research (grant 20-03-00716) and by the Ministry of Science and Higher Education of the Russian Federation (project FEUZ-2020-0052).
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Abstract
Regio- and stereoselective methods for the synthesis of 6′-trifluoro(trichloro)methyl substituted spiro[acenaphthylene-1,11′-chromeno[3,4-a](thia)pyrrolizidin]-2-ones and spiro[acenaphthylene-1,12′-chromeno[3,4-a]indolizidin]-2-ones have been developed based on the three-component reaction of 3-nitro-2-trifluoro(trichloro)methyl-2H-chromenes with azomethine ylides generated in situ from acenaphthenequinone and cyclic α-amino acids. The cycloaddition proceeds under mild conditions in ethanol or DMSO, and only endo-isomers of the products with cis-arrangement of nitro and trifluoromethyl groups are formed. The relative configuration of cycloadducts is reliably confirmed by X-ray diffraction analysis and by 2D NOESY spectroscopy.
Key words
3-nitro-2-trifluoro(trichloro)methyl-2H-chromenes - 1,3-dipolar cycloaddition - azomethine ylides - acenaphthenequinone - cyclic α-amino acidsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706005.
- Supporting Information
- CIF File
Publication History
Received: 13 November 2020
Accepted after revision: 05 December 2020
Article published online:
04 January 2021
© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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