CC BY-NC-ND 4.0 · SynOpen 2021; 05(01): 1-16
DOI: 10.1055/s-0040-1706005
paper

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

Igor B. Kutyashev
,
Maxim S. Sannikov
,
Ivan A. Kochnev
,
Alexey Y. Barkov
,
,
,
Vyacheslav Y. Sosnovskikh
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).


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.

Supporting Information



Publication History

Received: 13 November 2020

Accepted after revision: 05 December 2020

Article published online:
04 January 2021

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