Eco-friendly synthesis of fused pyrano[2,3-b]pyransviaammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds
Various substituted polycyclic pyrano[2,3-b]pyrans were synthesizedviathe condensation of 4H-chromene-3-carbaldehydes and their areno-condensed analogues with hetero- and carbocyclic 1,3-dicarbonyl compounds in acetic acid. Ammonium acetate was used as a green catalyst for the reaction. The process...
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Royal Society of Chemistry
2020
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ir-20.500.12258-145262020-10-22T12:42:26Z Eco-friendly synthesis of fused pyrano[2,3-b]pyransviaammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds Demidov, O. P. Демидов, О. П. Ammonia Condensation Equilibrium constants Gibbs free energy Organic polymers Rate constants Reaction intermediates Various substituted polycyclic pyrano[2,3-b]pyrans were synthesizedviathe condensation of 4H-chromene-3-carbaldehydes and their areno-condensed analogues with hetero- and carbocyclic 1,3-dicarbonyl compounds in acetic acid. Ammonium acetate was used as a green catalyst for the reaction. The process also involves the subsequent Knoevenagel condensation and 6π-electrocyclization of the 1-oxatriene intermediates formed. Fused pyridines were isolated as the products of the conjugated addition of ammonia to 1-oxatriene intermediates while using carbocyclic 1,3-dicarbonyl compounds and increasing the reaction time, indicating the reversibility of the electrocyclization stage. The calculated values of the Gibbs free energies and reaction rate constants for the 1-oxatriene - 2H-pyran equilibrium also testified to the irreversibility of pyrano[2,3-b]pyran formation in the case of using of heterocyclic 1,3-dicarbonyl compounds 2020-10-22T12:41:20Z 2020-10-22T12:41:20Z 2020 Статья Osyanin, V.A., Osipov, D.V., Semenova, I.A., Korzhenko, K.S., Lukashenko, A.V., Demidov, O.P., Klimochkin, Y.N. Eco-friendly synthesis of fused pyrano[2,3-b]pyransviaammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds // RSC Advances. - 2020. - Volume 10. - Issue 57. - Pages 34344-34354 http://hdl.handle.net/20.500.12258/14526 en RSC Advances application/pdf application/pdf Royal Society of Chemistry |
| institution |
СКФУ |
| collection |
Репозиторий |
| language |
English |
| topic |
Ammonia Condensation Equilibrium constants Gibbs free energy Organic polymers Rate constants Reaction intermediates |
| spellingShingle |
Ammonia Condensation Equilibrium constants Gibbs free energy Organic polymers Rate constants Reaction intermediates Demidov, O. P. Демидов, О. П. Eco-friendly synthesis of fused pyrano[2,3-b]pyransviaammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds |
| description |
Various substituted polycyclic pyrano[2,3-b]pyrans were synthesizedviathe condensation of 4H-chromene-3-carbaldehydes and their areno-condensed analogues with hetero- and carbocyclic 1,3-dicarbonyl compounds in acetic acid. Ammonium acetate was used as a green catalyst for the reaction. The process also involves the subsequent Knoevenagel condensation and 6π-electrocyclization of the 1-oxatriene intermediates formed. Fused pyridines were isolated as the products of the conjugated addition of ammonia to 1-oxatriene intermediates while using carbocyclic 1,3-dicarbonyl compounds and increasing the reaction time, indicating the reversibility of the electrocyclization stage. The calculated values of the Gibbs free energies and reaction rate constants for the 1-oxatriene - 2H-pyran equilibrium also testified to the irreversibility of pyrano[2,3-b]pyran formation in the case of using of heterocyclic 1,3-dicarbonyl compounds |
| format |
Статья |
| author |
Demidov, O. P. Демидов, О. П. |
| author_facet |
Demidov, O. P. Демидов, О. П. |
| author_sort |
Demidov, O. P. |
| title |
Eco-friendly synthesis of fused pyrano[2,3-b]pyransviaammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds |
| title_short |
Eco-friendly synthesis of fused pyrano[2,3-b]pyransviaammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds |
| title_full |
Eco-friendly synthesis of fused pyrano[2,3-b]pyransviaammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds |
| title_fullStr |
Eco-friendly synthesis of fused pyrano[2,3-b]pyransviaammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds |
| title_full_unstemmed |
Eco-friendly synthesis of fused pyrano[2,3-b]pyransviaammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds |
| title_sort |
eco-friendly synthesis of fused pyrano[2,3-b]pyransviaammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4h-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds |
| publisher |
Royal Society of Chemistry |
| publishDate |
2020 |
| url |
https://dspace.ncfu.ru/handle/20.500.12258/14526 |
| work_keys_str_mv |
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