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SECONDARY 3-AMINOTHIENO[2.3-b]PYRIDINE-2-CARBOXAMIDES IN REACTION WITH ortho-FORMYLBENZOIC ACID

В. К. Василин, Д. Ю. Лукина, Т. А. Строганова, П. Г. Морозов, Г. Д. Крапивин
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Abstract


By interaction of  secondary 3-aminothieno[2,3-b]pyridine-2-carboxamides with ortho-formylbenzoic acid angular (±)-7,7a-dihydropyrido[3",2":4',5']thieno[2',3':5,6] pypimido[2,1-a]isoindole-6,12-diones were obtained. In some cases, intermediate products − (±)-(1,2,3,4-tetrahydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-2-yl)benzoic acids − were separated from the reaction mixture.  It was shown that secondary  N-(5-methyl-2-furfuryl)carboxamides yield corresponding linear isoindole-6,8-diones in this reaction. The molecular structure one of the angular isoindole-6,12-diones was investigated by X-ray analysis.  Degenerate  intramolecular process of rotation in 7-arylisoindile-6,12-diones was studied by dynamic NMR.

How to Cite
Vasilin, V. K.; Lukina, D. Yu.; Stroganova, T. A.; Morozov, P. G.; Krapivin,G. D. Chem. Heterocycl. Compd. 2015, 50, 1756. [Khim. Geterotsikl. Soedin. 2014, 1908.]

For this article in the English edition see DOI 10.1007/s10593-015-1648-y


Keywords


3-aminothieno[2,3-b]pyridine-2-carboxamides; ortho-formylbenzoic acid; (±)-1,2,3,4-tetrahydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-2-yl)benzoic acids; (±)-7,7a-dihydropyrido[3'',2'':4',5']thieno[2',3':5,6]pyrimido[2,1-a]isoindole-6,12-diones; (±)-12b,13-dihydropyrido[3'',2'':4',5']thieno[3',2':4,5]pyrimido[2,1-a]isoindole-6,8-diones, X-ray analysis; intramolecular dynamics

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