Synthesis of 4-Nitro-N-phenyl-1,8-naphthalimide Annulated to Thia- and Azacrown Ether Moieties

Aleksander S. Oshchepkov; Maxim S. Oshchepkov; Antonina N. Arkhipova; Pavel A. Panchenko; Olga A. Fedorova

doi:10.1055/s-0036-1588712

Synthesis, Table of Contents

Synthesis 2017; 49(10): 2231-2240
DOI: 10.1055/s-0036-1588712

paper

Synthesis of 4-Nitro-N-phenyl-1,8-naphthalimide Annulated to Thia- and Azacrown Ether Moieties

Aleksander S. Oshchepkov

^aDepartment of Chemistry, M. V. Lomonosov State University, Vorobievi Gorii 1, Moscow 119991, Russian Federation Email: alexandr.oshch@mail.ru

,

Maxim S. Oshchepkov

^bD. Mendeleev University of Chemical Technology of Russia, Miusskaya Sqr., 9, 125047 Moscow, Russian Federation Email: maxim.os@mail.ru

,

Antonina N. Arkhipova

^cA. N. Nesmeyanov Institute of Organoelement compounds of RAS, Vavilova Str., 28, Moscow 119991, Russian Federation Email: fedorova@ineos.ac.ru

,

Pavel A. Panchenko

^bD. Mendeleev University of Chemical Technology of Russia, Miusskaya Sqr., 9, 125047 Moscow, Russian Federation Email: maxim.os@mail.ru

^cA. N. Nesmeyanov Institute of Organoelement compounds of RAS, Vavilova Str., 28, Moscow 119991, Russian Federation Email: fedorova@ineos.ac.ru

,

Olga A. Fedorova*

^aDepartment of Chemistry, M. V. Lomonosov State University, Vorobievi Gorii 1, Moscow 119991, Russian Federation Email: alexandr.oshch@mail.ru

^bD. Mendeleev University of Chemical Technology of Russia, Miusskaya Sqr., 9, 125047 Moscow, Russian Federation Email: maxim.os@mail.ru

^cA. N. Nesmeyanov Institute of Organoelement compounds of RAS, Vavilova Str., 28, Moscow 119991, Russian Federation Email: fedorova@ineos.ac.ru

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Abstract

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Abstract

Two convenient procedures for the synthesis of thia- and azacrown ether containing 4-nitro-1,8-naphthalimides have been developed. The first procedure is based on the amination of 1,8-naphthalic anhydride with crown-containing anilines. The second procedure includes the macrocyclization reaction of N-[1,2-bis(2-haloethoxy)phenyl]naphthalimide derivative with terminal thiols or methylamines. A strategy based on a macrocyclization is flexible and variable and also allows the use of the synthetic approach for more complex compounds.

Key words

azacrown ether - thiacrown ether - 1,8-naphthalimide - synthesis - macrocyclization

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References

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