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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Resumo

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.

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Sobre autores

E. Dikusar

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

Autor responsável pela correspondência
Email: evgen_58@mail.ru
ORCID ID: 0000-0002-3868-1871
Belarus, Minsk, 220072

E. 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. Zhukovskaya

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

Email: evgen_58@mail.ru
ORCID ID: 0000-0003-2795-4261
Rússia, Minsk, 220072

I. 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. 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. 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. Alekseeva

RUDN University

Email: evgen_58@mail.ru
ORCID ID: 0000-0001-6414-7122
Rússia, Moscow, 117198

N. Logvinenko

RUDN University

Email: evgen_58@mail.ru
ORCID ID: 0000-0001-8564-7353
Rússia, Moscow, 117198

D. Menshikova

RUDN University

Email: evgen_58@mail.ru
ORCID ID: 0000-0001-8642-1209
Rússia, Moscow, 117198

M. 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
Rússia, Moscow, 119071

V. 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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2. Fig. 1. General appearance of molecules of compounds 26 (a) and 36 (b) in a crystal.

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3. Fig. 2. Packing of molecules of compound 26 in a crystal.

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4. Fig. 3. Packing of molecules of compound 36 in a crystal.

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5. Scheme 1.

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6. Scheme 2.

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7. Scheme 3.

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8. Scheme 4.

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9. Additional files
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