Unusual behavior of 3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one towards some phosphorus reagents: Synthesis of novel diethyl 2-phosphonochromone, diethyl 3-phosphonopyrone and 1,3,2-oxathiaphosphinines
| Autor: | Heba Y. Zahran, Mohammed A. Assiri, Tarik E. Ali, I.S. Yahia |
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| Rok vydání: | 2019 |
| Předmět: |
Reaction mechanism
010405 organic chemistry Phosphorus Organic Chemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences Phosphonate Medicinal chemistry Pyrone 0104 chemical sciences chemistry.chemical_compound chemistry Elemental analysis Reagent Chromone Phosphorus tribromide |
| Zdroj: | Synthetic Communications. 49:550-557 |
| ISSN: | 1532-2432 0039-7911 |
| DOI: | 10.1080/00397911.2018.1560874 |
| Popis: | The chemical reactivity of 3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one (1) towards some phosphorus reagents was studied. The enaminone 1 was cyclized into diethyl 2-phosphonochromone 2 via its treatment with diethyl phosphite in basic medium. However, its reaction with triethoxy phosphonoacetate gave the substituted pyrone phosphonate 3. In addition, two novel examples of 4-(dimethylamino)-6-(2-hydroxyphenyl)-2-sulfido-4H-1,3,2-oxathia-phosphinines 6 and 7 were obtained from treatment of enaminone 1 with O,O-diethyl dithiophosphoric acid and Lawesson’s reagent. When enaminone 1 was also treated with phosphorus decasulfide, it was turned into 4H-thiochromene-4-thione while its treatment with phosphorus tribromide, phosphorus oxychloride, or phenylphosphonic dichloride, 4H-4-oxo-chromene was isolated in all cases. The possible reaction mechanisms of the formation of these products were discussed. The structures of newly isolated products were established by elemental analysis and spectral t... |
| Databáze: | OpenAIRE |
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