Please use this identifier to cite or link to this item: http://hdl.handle.net/10995/103078
Title: 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]-Cyclo addition Reaction
Authors: Kutyashev, I. B.
Sannikov, M. S.
Kochnev, I. A.
Barkov, A. Y.
Zimnitskiy, N. S.
Korotaev, V. Y.
Sosnovskikh, V. Y.
Issue Date: 2021
Publisher: Georg Thieme Verlag
Citation: 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]-Cyclo addition Reaction / I. B. Kutyashev, M. S. Sannikov, I. A. Kochnev, et al. — DOI 10.1055/s-0040-1706005 // SynOpen. — 2021. — Vol. 5. — Iss. 1. — so-2020-d0043-op.
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-2 H -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. © 2021 Georg Thieme Verlag. All rights reserved.
Keywords: 1,3-DIPOLAR CYCLOADDITION
3-NITRO-2-TRIFLUORO(TRICHLORO)METHYL- 2H -CHROMENES
ACENAPHTHENEQUINONE
AZOMETHINE YLIDES
CYCLIC Α-AMINO ACIDS
URI: http://hdl.handle.net/10995/103078
Access: info:eu-repo/semantics/openAccess
SCOPUS ID: 85101223697
PURE ID: 20520535
ISSN: 25099396
DOI: 10.1055/s-0040-1706005
metadata.dc.description.sponsorship: 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).
Appears in Collections:Научные публикации, проиндексированные в SCOPUS и WoS CC

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