Abstract
The reactions of 3-acetoxy-2-acetyl(cyanoacetyl)aminoisoindolin-1-one (1) with o-tosylaminobenzaldehyde and o-mesylaminobenzaldehyde morpholinals lead to a mixture of 2-(2-aminoquinoline-3-carboxamido)-3-morpholinoisoindolin-1-one (3) and 3-cyanoquinolin-2(1H)-one (4). The reaction of 1 with 5-nitro-2-tosylaminobenzaldehyde morpholinal yields a mixture of 2-(2-amino-6-nitroquinoline-carboxamido)-3-morpholinoisoindolin-1-one and 3-cyano-6-nitroquinolin-2(1H)-one. 3-Acetoxy-2-(quinolino[2,3-d]-2-methyl-4-oxopyrimidin-3-yl)isoindolin-1-one (20) was prepared by the condensation of o-formylbenzoic acid and 2-aminoquinoline-3-carbohydrazide in Ac2O. The structures of compounds 3, 4, and 20 were established by X-ray analysis.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 10002–1007, May, 2010.
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Ukhin, L.Y., Suponitskii, K.Y., Gribanova, T.N. et al. Synthesis of phthalimidines linked to quinoline derivatives by an amide bridge. Russ Chem Bull 59, 1023–1030 (2010). https://doi.org/10.1007/s11172-010-0199-8
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DOI: https://doi.org/10.1007/s11172-010-0199-8
Key words
- 3-acetoxy-2-acetyl(cyanoacetyl)aminoisoindolin-1-one
- morpholinals of o-tosylaminobenzaldehyde, o-mesylaminobenzaldehyde, 5-nitro-2-tosylaminobenzaldehyde
- 2-(2-aminoquinoline-3-carboxamido)-3-morpholinoisoindolin-1-one
- 3-cyanoquinolin-2(1H)-one
- 3-cyano-6-nitroquinolin-2(1H)-one
- 3-acetoxy-2-(quinolino[2,3-d]-2-methyl-4-oxopyrimidin-3-yl)isoindolin-1-one
- quantum chemical study, X-ray diffraction analysis