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Molbank, Vol. 2024, Article M1918: A Gram Scale Synthesis of 3,4-Dihalogen Substituted 1,8-Naphthalimides
Molbank doi: 10.3390/M1918
Authors: Denitsa Anastasova Monika Mutovska Natali Simeonova Irena Zagranyarska Zlatina Vlahova Stanimir Stoyanov Yulian Zagranyarski
A general protocol for the synthesis of 3,4-dihalogen substituted 1,8-naphthalimides is proposed, starting from available and cheap 1,8-naphthalic anhydride. The reported new compounds have only bromine or chlorine atoms as substituents, in contrast to the known iodo-containing analogues. This is an advantage in possible aryl nucleophilic substitution or cross-coupling modifications, making them interesting and important building-block molecules in naphthalimide chemistry. Although the procedure includes five synthetic steps, they are quick and straightforward. The overall yields are relatively high (48–62%), and only one column of chromatographic purification is needed. All the reactions were carried out on a multigram scale to allow the target building-block compounds to be obtained in sufficient amounts for further derivatizations.
