Izvestiya of Saratov University.

Chemistry. Biology. Ecology

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ISSN 2541-8971 (Online)

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Synthesis and Heterocyclization of 4-Hydroxy-3 - ((2-hydroxy-4,4-dimethyl-6-oxocyclohex1-en-1-yl) (aryl) methyl) -2H-chromen-2-ones

Kostritsky A. Yu., Saratov State University
Nakonechnikova Marina G., Saratov State University
Fedotova О. V., Saratov State University
Pchelintseva Nina V., Saratov State University

The possibility of obtaining asymmetric 1,5-diketones based on 4-hydroxy-2H-chromen-2-one and dimedone by three-component condensation in the presence of L-proline as a catalyst is shown. As a result, a series of 4-hydroxy3 - ((2-hydroxy-4,4-dimethyl-6-oxocyclohex1-en-1-yl) (aryl) methyl) -2H-chromen-2-ones was obtained with a yield of 25 up to 73%. The study revealed that the highest yield was observed for compounds containing fragments of ortho-substituted aldehydes capable of forming a hydrogen bond. For meta- and para-substituted – the lowest yield was observed. In the case of ortho-substitution this can be probably explained due to the stabilization of the intermediate complex by two intramolecular hydrogen bonds, which makes it possible to selectively obtain only one final product – 4-hydroxy-3 -((2-hydroxy4,4-dimethyl-6-oxocyclohex-1- en-1-yl) (aryl) methyl) -2Hchromen-2-one. The structure of the obtained products was confirmed by 1 H, 13C NMR, HSQC, HMBC spectroscopy. Considering the 1,5-diketone fragment for the above-described compounds, the possibility of their O-heterocyclization by propionic anhydride was suggested. Boiling 4-hydroxy-3 - ((2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl) (aryl) methyl) -2Hchromen-2-ones in anhydride medium for an hour resulted in obtaining a series of 7- (aryl) -10,10-dimethyl-7,9,10,11-tetrahydro-6H, 8H-chromeno [4,3-b] chromene-6,8-diones. Their structure was also confirmed by 1 H, 13C NMR, HSQC, HMBC spectroscopy.

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