4-Cyanomethyl- ortho -quinone tautomerism and the structure of the dienophile in Gates' morphine synthesis
| العنوان: | 4-Cyanomethyl- ortho -quinone tautomerism and the structure of the dienophile in Gates' morphine synthesis |
|---|---|
| المؤلفون: | Patrick A. Riley, Gnanamoly Yoganathan, Christopher A. Ramsden, Edward J. Land |
| المصدر: | Tetrahedron. 59:9547-9554 |
| بيانات النشر: | Elsevier BV, 2003. |
| سنة النشر: | 2003 |
| مصطلحات موضوعية: | ved/biology, Stereochemistry, Organic Chemistry, ved/biology.organism_classification_rank.species, Diastereomer, Biochemistry, Medicinal chemistry, Tautomer, Quinone, chemistry.chemical_compound, chemistry, Morpholine, Drug Discovery, Reactivity (chemistry), Acetonitrile, Derivative (chemistry), Conjugate acid |
| الوصف: | Oxidation of (3,4-dihydroxyphenyl)acetonitrile gives (3-hydroxy-4-oxo-cyclohexa-2,5-dienylidene)acetonitrile via the isomeric ortho -quinone ((3,4-dioxo-cyclohexa-2,5-dienylidene)acetonitrile). This para -quinomethane product is formed as a mixture of diastereoisomers and with an initial composition of Z / E 4:1. Over 24 h this mixture equilibrates to a composition of Z / E 5:4. The para -quinomethane reacts with morpholine to give (3,4-dihydroxyphenyl)-morpholin-4-yl-acetonitrile. Similar oxidation of (3,4-dihydroxynaphthalen-1-yl)acetonitrile also gives a para -quinomethane derivative and not the 1,2-naphthoquinone as previously described. The reactivity of this para -quinomethane derivative as a 1,3-dienophile in a key step of the Gates' morphine synthesis is attributed to formation of its conjugate acid. |
| تدمد: | 0040-4020 |
| DOI: | 10.1016/j.tet.2003.10.008 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::a8d154dd9ce7d6d4007e57b50ca5ebd0 https://doi.org/10.1016/j.tet.2003.10.008 |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi...........a8d154dd9ce7d6d4007e57b50ca5ebd0 |
| قاعدة البيانات: | OpenAIRE |
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