Advanced Synthesis and Catalysis, volume 364, issue 15, pages 2557-2564
Synthesis of Bis(β‐Oximinoalkyl)malonates and Their Catalytic Reductive Cyclization to Piperidines
3
UIUC: Roger Adams Laboratory Department of Chemistry University of Illinois Urbana Illinois, 61801 United States
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Publication type: Journal Article
Publication date: 2022-07-12
Journal:
Advanced Synthesis and Catalysis
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.4
ISSN: 16154150, 16154169
Catalysis
Organic Chemistry
Abstract
Hitherto unknown bis(β‐oximinoalkyl)malonates were demonstrated to be convenient platforms for the synthesis of saturated N‐heterocycles. Upon heterogeneous catalytic hydrogenation, these dioximes undergo reductive cyclization to give substituted piperidine‐4,4’‐dicarboxylates, which are valuable building blocks in medicinal chemistry. By using dioximes bearing an additional ester group in the side chain, tandem piperidine/pyrrolidinone ring closure leading to indolizidinone framework was showcased in this work. A modular synthesis of initial bis(β‐oximinoalkyl)malonates (both symmetrically and unsymmetrically substituted) was accomplished via a sequential Michael addition of two nitrosoalkene molecules to malonic ester. The mechanism of the reductive cyclization of dioximes to piperidines was investigated by isotope scrambling experiments and isolation of intermediates.
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1 publication, 16.67%
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Springer Nature
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Springer Nature
1 publication, 16.67%
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- We do not take into account publications that without a DOI.
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Pospelov E. V. et al. Synthesis of Bis(β‐Oximinoalkyl)malonates and Their Catalytic Reductive Cyclization to Piperidines // Advanced Synthesis and Catalysis. 2022. Vol. 364. No. 15. pp. 2557-2564.
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Pospelov E. V., Boyko Y. D., Ioffe S. L., Sukhorukov A. Yu. Synthesis of Bis(β‐Oximinoalkyl)malonates and Their Catalytic Reductive Cyclization to Piperidines // Advanced Synthesis and Catalysis. 2022. Vol. 364. No. 15. pp. 2557-2564.
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TY - JOUR
DO - 10.1002/adsc.202200424
UR - https://doi.org/10.1002%2Fadsc.202200424
TI - Synthesis of Bis(β‐Oximinoalkyl)malonates and Their Catalytic Reductive Cyclization to Piperidines
T2 - Advanced Synthesis and Catalysis
AU - Boyko, Yaroslav D
AU - Ioffe, Sema L
AU - Pospelov, Evgeny V
AU - Sukhorukov, Alexey Yu
PY - 2022
DA - 2022/07/12 00:00:00
PB - Wiley
SP - 2557-2564
IS - 15
VL - 364
SN - 1615-4150
SN - 1615-4169
ER -
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@article{2022_Pospelov,
author = {Yaroslav D Boyko and Sema L Ioffe and Evgeny V Pospelov and Alexey Yu Sukhorukov},
title = {Synthesis of Bis(β‐Oximinoalkyl)malonates and Their Catalytic Reductive Cyclization to Piperidines},
journal = {Advanced Synthesis and Catalysis},
year = {2022},
volume = {364},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002%2Fadsc.202200424},
number = {15},
pages = {2557--2564},
doi = {10.1002/adsc.202200424}
}
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Pospelov, Evgeny V., et al. “Synthesis of Bis(β‐Oximinoalkyl)malonates and Their Catalytic Reductive Cyclization to Piperidines.” Advanced Synthesis and Catalysis, vol. 364, no. 15, Jul. 2022, pp. 2557-2564. https://doi.org/10.1002%2Fadsc.202200424.
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