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Efficient Synthesis of 2-Substituted Phthalimides from Phthalic Acids in One Step
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Medicine, Department of Public Health and Clinical Medicine, Medicine.
2013 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2013, no 33, 7512-7516 p.Article in journal (Refereed) Published
Abstract [en]

Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The phthalimide central fragment frequently appears in biologically active compounds, materials, catalysts, and fluorescent probes, and therefore the development of general, fast, and convenient synthetic methods to this scaffold under neutral, acidic, and basic conditions would be attractive. After an initial screening, the use of acetonitrile, acetic acid, or pyridine in combination with microwave heating proved most promising. Experimental design was applied to these conditions to optimize the time, temperature, and concentration. This strategy has successfully generated synthetic methods that have been used to synthesize a series of phthalimides from phthalic acids and various amines or anilines in excellent yields. The developed methods have proven to be general, fast, convenient, and economic, and thus are expected to have broad utility to efficiently construct novel compounds for future biological and chemical applications.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2013. Vol. 2013, no 33, 7512-7516 p.
Keyword [en]
Oxygen heterocycles, Nitrogen heterocycles, Experimental design, Microwave chemistry
National Category
Organic Chemistry
URN: urn:nbn:se:umu:diva-84123DOI: 10.1002/ejoc.201300952ISI: 000326968100011OAI: diva2:680268
Available from: 2013-12-17 Created: 2013-12-16 Last updated: 2013-12-17Bibliographically approved

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