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Development and optimization of simple one-step methods for the synthesis of 4-amino-substituted 1,8-naphthalimides
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Medicine, Department of Public Health and Clinical Medicine, Medicine.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
2014 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 28, 6175-6182 p.Article in journal (Refereed) Published
Abstract [en]

The 1,8-naphthalimide central fragment can be found in a vast number of bioactive compounds and drugs in clinical trials, and can be recognized from their use as fluorescent probes. Of key importance for the fluorescent properties of the scaffold is the 4-amino substituent, which has also proven to be critical in several other chemical and biological applications. Because of the great interest in 1,8-naphthalimides in general, and 4-amino-substituted 1,8-naphthalimides in particular, we have developed and optimized one-step procedures with which to access these derivatives by using an experimental design approach. The multivariate studies of temperature, reaction time, and equivalents of substrates identified conditions with close to quantitative yields that could be applied to generate a range of 4-amino-substituted 1,8-naphthalimides in high yields.

Place, publisher, year, edition, pages
2014. no 28, 6175-6182 p.
Keyword [en]
Oxygen heterocycles, Multicomponent reactions, Nitrogen heterocycles, Synthetic methods, crowave chemistry
National Category
Organic Chemistry
URN: urn:nbn:se:umu:diva-95868DOI: 10.1002/ejoc.201402684ISI: 000342842500008OAI: diva2:770939
Available from: 2014-12-11 Created: 2014-11-06 Last updated: 2015-12-16Bibliographically approved

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