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2-SUBSTITUTED 3-NITRO-2H-CHROMENES IN REACTION WITH AZOMETHINE YLIDE DERIVED FROM NINHYDRIN AND PROLINE: REGIO- AND STEREOSELECTIVE SYNTHESIS OF SPIRO[CHROMENO¬[3,4-a]PYRROLIZIDINE-11,2'-INDE¬NE]-1',3'-DIONES

Владислав Юрьевич Коротаев, Игорь Б. Кутяшев, Алексей Ю. Барков, Вячеслав Я. Сосновских
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Abstract


Regio- and stereoselective 1,3-dipolar cycloaddition of stabilized azomethine ylides, generated in situ from ninhydrin and proline, occurred at the double bond activated by nitro group in 3-nitro-2-(trifluoromethyl)- and 3-nitro-2-phenyl-2H-chromenes upon heating in ethanol. This reaction produced high yields of spiro[chromeno[3,4-a]pyrrolizidine-11,2'-indene]-1',3'-diones. The structure of the obtained products was confirmed by the method of X-ray crystallography.

 


Keywords


3-nitro-2H-chromenes, spiro[chromeno[3,4-a]pyrrolizidine-11,2'-indene]-1',3'-diones, stabilized azomethine ylides, 1,3dipolar cycloaddition.

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