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Kostritsky А. Y., Nakonechnikova M. G., Fedotova О. V., Pchelintseva N. V. Synthesis and Heterocyclization of 4-Hydroxy-3 - ((2-hydroxy-4,4-dimethyl-6-oxocyclohex1-en-1-yl) (aryl) methyl) -2H-chromen-2-ones. Izvestiya of Saratov University. Chemistry. Biology. Ecology, 2020, vol. 20, iss. 4, pp. 362-371. DOI: https://doi.org/10.18500/1816-9775-2020-20-4-362-371


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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

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RAR научная статья
Abstract

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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