Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

• Zbigniew Malinowski,
• Emilia Fornal,
• Agata Sumara,
• Renata Kontek,
• Karol Bukowski,
• Beata Pasternak,
• Dariusz Sroczyński,
• Joachim Kusz,
• Magdalena Małecka and
• Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

• )-ones 3a–d were prepared in two steps starting from phthalazin-1(2H)-one (1). The 4-bromo-derivative 2 was synthesized directly from lactam 1, which underwent the selective bromination at the 4-position using the combination of Br2 and KBr (KBr3) in acetate buffer, following the method previously

• observed. Instead, the partial demethylation of the amine occurred. As a result, a mixture of the products 6c and 6d (molar ratio 6c/6d = 1:4) was obtained. With the increase in the amount of palladium (15 mol %) the phthalazin-1(2H)-one derivative 6d was obtained as the main product (70%). Complexation

• In conclusion, we have demonstrated an efficient synthesis of 2-substituted (alkyl, aminoalkyl) 4-aminophthalazinones 5 and 6 via the direct bromination of phthalazin-1(2H)-one (1) with potassium tribromide, followed by the alkylation of 4-bromophthalazinone 2 with methyl iodide, isopropyl iodide or

The facile construction of the phthalazin-1(2H)-one scaffold via copper-mediated C–H(sp²)/C–H(sp) coupling under mild conditions

• Wei Zhu,
• Bao Wang,
• Shengbin Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2015, 11, 1624–1631, doi:10.3762/bjoc.11.177

• Wei Zhu Bao Wang Shengbin Zhou Hong Liu CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. China 10.3762/bjoc.11.177 Abstract A novel strategy for the construction of the phthalazin-1(2H)-one

• conditions. Through the removal of the directing group, the resulting moiety could easily be transformed into the phthalazin-1(2H)-one scaffold, which is known to be a privileged moiety and a bioactive nucleus in pharmaceuticals. Keywords: C–H activation; copper; phthalazin-1(2H)-one; Introduction The

• phthalazin-1(2H)-one scaffold represents an important class of privileged structures and has been widely found in numerous biologically active compounds and drug molecules [1][2][3][4][5][6]. For example (Figure 1), azelastine is a selective histamine antagonist, which is recommended for the treatment of