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Secondary 3-Aminothieno[2,3-b]Pyridine-2-Carboxamides in Reaction with ortho-Formylbenzoic Acid

The reaction of secondary 3-aminothieno[2,3-b]pyridine-2-carboxamides with ortho-formylbenzoic acid gave angular (±)-7,7a-dihydropyrido[3",2":4',5']thieno[2',3':5,6]pyrimido[2,1-a]isoindole-6,12-diones. The intermediate products, (±)-(1,2,3,4-tetrahydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-2-yl)benzoic acids, were isolated in some cases. Secondary N-[(5-methylfuran-2-yl)methyl]carboxamides were shown to form linear isoindole-6,8-diones in this reaction. One of the angular isoindole-6,12-dione derivatives was studied by X-ray structural analysis. Dynamic NMR was used to characterize the degenerate intramolecular rotation in molecules of isoindole-6,12-diones.

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Correspondence to G. D. Krapivin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1908–1919, December, 2014.

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Vasilin, V.K., Lukina, D.Y., Stroganova, T.A. et al. Secondary 3-Aminothieno[2,3-b]Pyridine-2-Carboxamides in Reaction with ortho-Formylbenzoic Acid. Chem Heterocycl Comp 50, 1756–1767 (2015).

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