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DIFFERENT BEHAVIOR OF AZOMETHINE YLIDES DERIVED FROM 11H-INDENO[1,2-b]QUINOXALIN-11-ONE AND PROLINE/SARCOSINE IN REACTIONS WITH 3-NITRO-2H-CHROMENES

Игорь Б. Кутяшев, Алексей Ю. Барков, Николай С. Зимницкий, Владислав Ю. Коротаев, Вячеслав Я. Сосновских
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Abstract


(3+2) Cycloaddition of azomethine ylide generated in situ from 11H-indeno[1,2-b]quinoxalin-11-one and proline to 3-nitro-2-trifluoro(trichloro)methyl- and 3-nitro-2-phenyl-2H-chromenes upon heating in EtOH proceeded regio- and stereoselectively, resulting in the formation of spiro[chromeno[3,4-a]pyrrolizine-11,11'-indeno[1,2-b]quinoxalines]. An analogous reaction using ylide derived from sarcosine under the conditions of kinetic control led to preferential formation of diastereomeric spiro[chromeno[3,4-c]pyrrolidine-3,11'-indeno[1,2-b]quinoxalines] with different configuration of the spiro atom, which were transformed upon heating in DMSO into the thermodynamically more stable spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines].

Keywords


azomethine ylides, 11H-indeno[1,2-b]quinoxalin-11-one, 3-nitro-2H-chromenes, proline, sarcosine, spirochromeno[3,4-c]pyrrolidines, spirochromeno[3,4-a]pyrrolizidines, (3+2) cycloaddition

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