Amination, Acetamidation, and Amidation of Substituted Aromatic Carbamates in Polyphosphoric Acid
العنوان: | Amination, Acetamidation, and Amidation of Substituted Aromatic Carbamates in Polyphosphoric Acid |
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المؤلفون: | N. N. Stepkina, E. N. Kutlalieva, E. A. Shustova, A. V. Velikorodov, O. Yu. Poddubny |
المصدر: | Russian Journal of Organic Chemistry. 56:1570-1575 |
بيانات النشر: | Pleiades Publishing Ltd, 2020. |
سنة النشر: | 2020 |
مصطلحات موضوعية: | Carbamate, Ortho position, Nitromethane, 010405 organic chemistry, organic chemicals, medicine.medical_treatment, Organic Chemistry, 01 natural sciences, Medicinal chemistry, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Electrophilic amination, medicine, Nitroethane, Sodium azide, heterocyclic compounds, Amination, Benzoic acid |
الوصف: | Electrophilic amination of methyl N-(hydroxyphenyl)carbamates and methyl N-(4-methoxyphenyl)carbamate with sodium azide in 86% polyphosphoric acid (PPA) at 55–60°C regioselectively afforded methyl N-(3-amino-2-hydroxyphenyl)-, N-(4-amino-3-hydroxyphenyl)-, N-(3-amino-4-hydroxyphenyl)-, and N-(3-amino-4-methoxyphenyl)carbamates, i.e., the amino group entered the ortho position with respect to the hydroxy or methoxy group. The reactions of methyl N-(4-methoxyphenyl)carbamate with nitromethane and nitroethane in 80% PPA at 95–110°C gave methyl N-(3-carbamoyl-4-methoxyphenyl)carbamate and methyl N-(3-acetamido-4-methoxyphenyl)carbamate, respectively. Methyl N-[4-(N′-hydroxyethanimidamido)phenyl]carbamate was obtained by reaction of 4-[(methoxycarbonyl)amino]benzoic acid with excess nitroethane in 86% PPA at 125°C. |
تدمد: | 1608-3393 1070-4280 |
URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::19c2de0e4dd5e0a88b5b264c857e8e25 https://doi.org/10.1134/s1070428020090110 |
حقوق: | CLOSED |
رقم الأكسشن: | edsair.doi...........19c2de0e4dd5e0a88b5b264c857e8e25 |
قاعدة البيانات: | OpenAIRE |
تدمد: | 16083393 10704280 |
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