Email this article Synthesis and some transformations of new acetophenones with carbamate function
- Authors: Velikorodov A.V1,2, Kutlalieva E.N1,2, Nosachev S.B1, Shustova E.A2
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Affiliations:
- Astrakhan State University
- Astrakhan State Medical University
- Issue: Vol 59, No 1 (2023)
- Pages: 97-105
- Section: Articles
- URL: https://bakhtiniada.ru/0514-7492/article/view/144712
- DOI: https://doi.org/10.31857/S0514749223010081
- EDN: https://elibrary.ru/PFYQZU
- ID: 144712
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Abstract
Acylation of methyl- N -phenyl-, 2-(morpholin-4-yl)ethylphenyl-, 2-(pyridin-2-yl)ethylphenyl-carbamates with acetic anhydride in polyphosphoric acid at 50-55°C for 3 h proceeds in the para -position to the carbamate grouping to form the corresponding acetophenones. Acylation under similar conditions of methyl 2-(methoxyphenyl)carbamate occurs in the para -position to the methoxy group with the formation of methyl N -(5-acetyl-2-methoxyphenyl)carbamate. The interaction of para - and ortho -acetyl-substituted methyl- N -phenylcarbamate with N -bromosuccinimide, copper(II) acetate in the presence of dimethylformamide at 80°C and with chloro- and hydrobromic acids in the presence of DMSO in ethyl acetate at 30-33°C yielded methyl {4(2)-[(dimethylamino)(oxo)-acetyl]phenyl}- and N -[4(2)-(2-bromo-2-chloroacetyl)phenyl]-carbamates. Condensation of 2-morpholinoethyl [(pyridin-2-yl)ethyl] N -(4-acetylphenyl)carbamates with 4-methoxybenzaldehyde in the presence of a methanolic KOH solution gave the corresponding chalcones.
About the authors
A. V Velikorodov
Astrakhan State University;Astrakhan State Medical University
Email: avelikorodov@mail.ru
E. N Kutlalieva
Astrakhan State University;Astrakhan State Medical University
Email: avelikorodov@mail.ru
S. B Nosachev
Astrakhan State University
Email: avelikorodov@mail.ru
E. A Shustova
Astrakhan State Medical University
Email: avelikorodov@mail.ru
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