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Unexpected hydrazine- and hydroxylamine-induced transformations of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety

Dat T Nguyen 1
Dat T Nguyen
, 
Hieu Hong Truong 2
Hieu Hong Truong
, 
Nhung Thi Dao 1
Nhung Thi Dao
, 
Van T.T. Tran 1
Van T.T. Tran
, 
Olga Sergeevna Gorchakova 3
Olga Sergeevna Gorchakova
, 
Anh Tuan Le 1
Anh Tuan Le
1 Faculty of Chemistry, University of Science, Vietnam National University, Hanoi, Hoan Kiem, Hanoi, Vietnam
2 Peoples Friendship University of Russia (RUDN University), Moscow, Russian Federation
3 'Sanofi-aventis group' Representative office in Russia, Moscow, Russian Federation
10.1016/j.mencom.2023.09.037
Published 2023-09-01
Communication , Volume 33, Issue 5, 708-710
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Nguyen D. T. et al. Unexpected hydrazine- and hydroxylamine-induced transformations of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 708-710.
GOST all authors (up to 50) Copy
Nguyen D. T., Truong H. H., Dao N. T., Tran V. T., Gorchakova O. S., Le A. T. Unexpected hydrazine- and hydroxylamine-induced transformations of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 708-710.
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TY - JOUR
DO - 10.1016/j.mencom.2023.09.037
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.037
TI - Unexpected hydrazine- and hydroxylamine-induced transformations of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety
T2 - Mendeleev Communications
AU - Nguyen, Dat T
AU - Truong, Hieu Hong
AU - Dao, Nhung Thi
AU - Tran, Van T.T.
AU - Gorchakova, Olga Sergeevna
AU - Le, Anh Tuan
PY - 2023
DA - 2023/09/01
PB - Mendeleev Communications
SP - 708-710
IS - 5
VL - 33
ER -
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@article{2023_Nguyen,
author = {Dat T Nguyen and Hieu Hong Truong and Nhung Thi Dao and Van T.T. Tran and Olga Sergeevna Gorchakova and Anh Tuan Le},
title = {Unexpected hydrazine- and hydroxylamine-induced transformations of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.037},
number = {5},
pages = {708--710},
doi = {10.1016/j.mencom.2023.09.037}
}
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Nguyen, Dat T., et al. “Unexpected hydrazine- and hydroxylamine-induced transformations of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety.” Mendeleev Communications, vol. 33, no. 5, Sep. 2023, pp. 708-710. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.037.

Keywords

azacrown ether
cyclopenteno-13-crown-3 ether.
hydrazone
Nazarov reaction
piperidone

Abstract

Reactions of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety with hydrazine and hydroxylamine proceed at the functional groups. One unexpected product, cyclopenteno-13-crown-3 ether derivative, is formed when hydrazine hydrochloride is used, its formation occurring via deamination of the piperidine followed by the Nazarov reaction of the intermediate hydrazono diene. According to the QSAR through ADMET calculation, the synthesized compounds may show high potential for biological studies.

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