Amination, Acetamidation, and Amidation of Substituted Aromatic Carbamates in Polyphosphoric Acid

التفاصيل البيبلوغرافية
العنوان: Amination, Acetamidation, and Amidation of Substituted Aromatic Carbamates in Polyphosphoric Acid
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