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Synthesis of phthalimidines linked to quinoline derivatives by an amide bridge

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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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Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp. Stachki, 344090, Rostov-on-Don, Russian Federation

    L. Yu. Ukhin, T. N. Gribanova & L. V. Belousova

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    K. Yu. Suponitskii

  3. Southern Scientific Center, Russian Academy of Sciences, 41 ul. Chekhova, 344006, Rostov-on-Don, Russian Federation

    E. N. Shepelenko

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  1. L. Yu. Ukhin
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  2. K. Yu. Suponitskii
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  3. T. N. Gribanova
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  4. L. V. Belousova
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  5. E. N. Shepelenko
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Correspondence to L. Yu. Ukhin.

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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

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