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The unusual reaction of 2-isocyanatophenyl acetate with amines and water

Boris Pavlovich Gladkikh 1
Boris Pavlovich Gladkikh
, 
Vladimir Sergeevich D'yachenko 1, 2
Vladimir Sergeevich D'yachenko
, 
Vladimir Vladimirovich Burmistrov 1, 2
Vladimir Vladimirovich Burmistrov
, 
Gennady Mikhailovich Butov 1, 2
Gennady Mikhailovich Butov
, 
10.1016/j.mencom.2022.09.039
Published 2022-09-05
Communication , Volume 32, Issue 5, 683-685
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Gladkikh B. P. et al. The unusual reaction of 2-isocyanatophenyl acetate with amines and water // Mendeleev Communications. 2022. Vol. 32. No. 5. pp. 683-685.
GOST all authors (up to 50) Copy
Gladkikh B. P., D'yachenko V. S., Burmistrov V. V., Butov G. M., Novakov I. A. The unusual reaction of 2-isocyanatophenyl acetate with amines and water // Mendeleev Communications. 2022. Vol. 32. No. 5. pp. 683-685.
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TY - JOUR
DO - 10.1016/j.mencom.2022.09.039
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.09.039
TI - The unusual reaction of 2-isocyanatophenyl acetate with amines and water
T2 - Mendeleev Communications
AU - Gladkikh, Boris Pavlovich
AU - D'yachenko, Vladimir Sergeevich
AU - Burmistrov, Vladimir Vladimirovich
AU - Butov, Gennady Mikhailovich
AU - Novakov, Ivan Aleksandrovich
PY - 2022
DA - 2022/09/05
PB - Mendeleev Communications
SP - 683-685
IS - 5
VL - 32
ER -
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@article{2022_Gladkikh,
author = {Boris Pavlovich Gladkikh and Vladimir Sergeevich D'yachenko and Vladimir Vladimirovich Burmistrov and Gennady Mikhailovich Butov and Ivan Aleksandrovich Novakov},
title = {The unusual reaction of 2-isocyanatophenyl acetate with amines and water},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.09.039},
number = {5},
pages = {683--685},
doi = {10.1016/j.mencom.2022.09.039}
}
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Gladkikh, Boris Pavlovich, et al. “The unusual reaction of 2-isocyanatophenyl acetate with amines and water.” Mendeleev Communications, vol. 32, no. 5, Sep. 2022, pp. 683-685. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.09.039.

Keywords

2-benzoxazolinone
2-isocyanatophenyl acetate
acetamides
acetylsalicylic acid
ureas

Abstract

The reaction of 2-isocyanatophenyl acetate with adamantyl and phenyl-containing amines gave the corresponding acetamides. Intermediate 2-isocyanatophenol formed in the course of the reaction undergoes intramolecular cyclization to 2-benzoxazolinone. These reactions proceed only with amines possessing basicity (pKb > 3.80).

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