Synthesis 2017; 49(10): 2231-2240
DOI: 10.1055/s-0036-1588712
paper
© Georg Thieme Verlag Stuttgart · New York

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

Aleksander S. Oshchepkov
a   Department of Chemistry, M. V. Lomonosov State University, Vorobievi Gorii 1, Moscow 119991, Russian Federation   Email: alexandr.oshch@mail.ru
,
Maxim S. Oshchepkov
b   D. Mendeleev University of Chemical Technology of Russia, Miusskaya Sqr., 9, 125047 Moscow, Russian Federation   Email: maxim.os@mail.ru
,
Antonina N. Arkhipova
c   A. N. Nesmeyanov Institute of Organoelement compounds of RAS, Vavilova Str., 28, Moscow 119991, Russian Federation   Email: fedorova@ineos.ac.ru
,
Pavel A. Panchenko
b   D. Mendeleev University of Chemical Technology of Russia, Miusskaya Sqr., 9, 125047 Moscow, Russian Federation   Email: maxim.os@mail.ru
c   A. N. Nesmeyanov Institute of Organoelement compounds of RAS, Vavilova Str., 28, Moscow 119991, Russian Federation   Email: fedorova@ineos.ac.ru
,
Olga A. Fedorova*
a   Department of Chemistry, M. V. Lomonosov State University, Vorobievi Gorii 1, Moscow 119991, Russian Federation   Email: alexandr.oshch@mail.ru
b   D. Mendeleev University of Chemical Technology of Russia, Miusskaya Sqr., 9, 125047 Moscow, Russian Federation   Email: maxim.os@mail.ru
c   A. N. Nesmeyanov Institute of Organoelement compounds of RAS, Vavilova Str., 28, Moscow 119991, Russian Federation   Email: fedorova@ineos.ac.ru
› Author Affiliations
Further Information

Publication History

Received: 02 November 2016

Accepted after revision: 20 January 2017

Publication Date:
14 February 2017 (online)


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.

Supporting Information

 
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