Synthesis of Formylphenyl 1-Oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylates and Their (E)-1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-yliminomethyl Derivatives

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Abstract

Formylphenyloxohydroepoxyisoindole carboxylates were prepared by the reaction of 4-hydroxy-3-methoxy-, 4-hydroxy-3-ethoxy- and 3-hydroxy-4-methoxybenzaldehydes with substituted isoindolecarboxylic acids {2-methyl-1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic, 2-(3,4-dimethoxyphenethyl)1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic, 2-(benzo[d][1,3]dioxol-5-ylmethyl)-1-oxo1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic, 6-oxo-3,4,6,6a,7,8-hexahydro-2H,10bH-8,10a-epoxy[1,3]oxazino[2,3-a]isoindole-7-carboxylic, 2-(2,3-dichlorobenzyl)-1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic} in dichloromethane in the presence of dicyclohexylcarbodiimide. The corresponding (E)-azomethines were synthesized by condensation of formylphenyloxohydroepoxyisoindole carboxylates with 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one in methanol.

About the authors

E. A. Dikusar

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

Author for correspondence.
Email: evgen_58@mail.ru
ORCID iD: 0000-0002-3868-1871
Belarus, Minsk, 220072

E. A. Akishina

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

Email: evgen_58@mail.ru
ORCID iD: 0000-0002-0803-8623
Belarus, Minsk, 220072

N. A. Zhukovskaya

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

Email: evgen_58@mail.ru
ORCID iD: 0000-0003-2795-4261
Russian Federation, Minsk, 220072

I. A. Kolesnik

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

Email: evgen_58@mail.ru
ORCID iD: 0000-0003-4921-4299
Belarus, Minsk, 220072

E. N. Margun

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

Email: evgen_58@mail.ru
ORCID iD: 0009-0002-4843-3916
Belarus, Minsk, 220072

S. S. Kovalskaya

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

Email: evgen_58@mail.ru
ORCID iD: 0009-0002-3445-2809
Belarus, Minsk, 220072

K. A. Alekseeva

RUDN University

Email: evgen_58@mail.ru
ORCID iD: 0000-0001-6414-7122
Russian Federation, Moscow, 117198

N. A. Logvinenko

RUDN University

Email: evgen_58@mail.ru
ORCID iD: 0000-0001-8564-7353
Russian Federation, Moscow, 117198

D. I. Menshikova

RUDN University

Email: evgen_58@mail.ru
ORCID iD: 0000-0001-8642-1209
Russian Federation, Moscow, 117198

M. S. Grigoriev

Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences

Email: evgen_58@mail.ru
ORCID iD: 0000-0002-6363-5535
Russian Federation, Moscow, 119071

V. I. Potkin

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

Email: evgen_58@mail.ru
ORCID iD: 0000-0003-0250-837X
Belarus, Minsk, 220072

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