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SM ISO690:2012 POGREBNOI, Vsevolod, STYNGACH, Evgenia, SUCMAN, Natalia, MAKAEV, Fliur. The first example of spirocyclopropaneoxindole functionalized by dehydroabietic acid. In: Achievements and perspectives of modern chemistry, 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 235. ISBN 978-9975-62-428-2. |
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Achievements and perspectives of modern chemistry 2019 | ||||||
Conferința "International Conference "Achievements and perspectives of modern chemistry"" Chişinău, Moldova, 9-11 octombrie 2019 | ||||||
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Pag. 235-235 | ||||||
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Oxindolic fragment is an often part of many natural compounds having various useful biological properties such as antiviral, anti-cancer, antimicrobial etc. It is worth noting and different spirooxindoles, because the presence of spirocycle in its molecules, its scale and variety of substitutes in spirocycles lead us to a huge amount of substances with potential biologic activity. It is known, that spirocyclopropaneoxindoles possessing anti-HIV activity, that is why, the synthesis of such optically pure compounds is a very good challenge.formulaInitially, the selective extraction from turpentine succeeding by uneasy processes leads us to pure [1] dehydroabietic acid 1, but the next interaction with oxalylchloride in dry chloroform gave us chloride 2 in quantitative yield practically. The synthesis of cyclopropaneoxindole 4 resulted in four stages [2, 3] (see scheme), but the final conversion was realized by classical amidation reaction between chloride 2 and oxindole 4 in dry chloroform with equimolar amount of Et3N and led us to new functionalized spirocyclopropaneoxindole 3. The target compound was isolated by column chromatography and proved by NMR. |
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