DIFFERENT BEHAVIOR OF AZOMETHINE YLIDES DERIVED FROM 11<i>H</i>-INDENO[1,2-<i>b</i>]QUINOXALIN-11-ONE AND PROLINE/SARCOSINE IN REACTIONS WITH 3-NITRO-2<i>H</i>-CHROMENES
Authors
Игорь Б. Кутяшев
Institute of Natural Sciences and Mathematics,
Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
Алексей Ю. Барков
Institute of Natural Sciences and Mathematics,
Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
Николай С. Зимницкий
Institute of Natural Sciences and Mathematics,
Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
Владислав Ю. Коротаев
Institute of Natural Sciences and Mathematics,
Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
Вячеслав Я. Сосновских
Institute of Natural Sciences and Mathematics,
Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
(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].
