SYNTHESIS AND STRUCTURE OF ESTERIFICATION PRODUCTS OF 6-ARYL-1,2,3,6,7,7а-HEXAHYDRO-3а,6-EPOXYISOINDOLE-7-CARBOXYLIC ACIDS
Authors
Марьяна А. Надирова
Institute of Organic and Macromolecular Chemistry, Heinrich Heine University Düsseldorf, 1 Universitäts St., Düsseldorf 40225, Germany
Кузьма М. Показеев
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova St., Minsk 220072, Belarus
Ирина А. Колесник
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova St., Minsk 220072, Belarus
Павел В. Дороватовский
National Research Center ''Kurchatov Institute'',
1 Akademika Kurchatova Sq., Moscow 123182, Russia
Николай А. Бумагин
M. V. Lomonosov Moscow State University,
1 Build. 3, Leninskie Gory, Moscow 119991, Russia
Владимир И. Поткин
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova St., Minsk 220072, Belarus
It was found that the reaction of 5-arylfurfurilamines with maleic anhydride leads to the formation of 6-aryl-3a,6-epoxyisoindole-7-carboxylic acids (the cyclic form), which in solution are in dynamic equilibrium with N-furfurylmaleinamides (the open form). During the esterification of these tautomeric mixtures with methanol in the presence of a catalytic amount of sulfuric acid, methyl esters of 5-aryl-7a-hydroxy-7-methoxy-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindole-4-carboxylic acids, unexpected cleavage products of the 3a,6-oxobridge of the cyclic form, are formed diastereospecifically. The structure of the obtained products was confirmed by X-ray structural analysis.
Author Biography
Николай А. Бумагин, M. V. Lomonosov Moscow State University,
1 Build. 3, Leninskie Gory, Moscow 119991, Russia
Ведущий научный сотрудник кафедры органической химии, доктор химических наук, профессор
