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Cycloaddition of Huisgen 1,4-dipoles: Synthesis and rapid epimerization of functionalized spiropyrido[2,1-: B] [1,3]oxazine-pyrroles and related products
Publication type: Journal Article
Publication date: 2022-01-01
scimago Q1
wos Q2
SJR: 0.777
CiteScore: 7.6
Impact factor: 4.6
ISSN: 20462069
PubMed ID:
35424489
General Chemistry
General Chemical Engineering
Abstract
1,4-Dipolar cycloaddition has emerged as a powerful tool for the synthesis of various cyclic compounds. In the present work, 1H-pyrrole-2,3-diones are proposed as new dipolarophiles for 1,4-dipolar cycloaddition. Their [4 + 2] cycloaddition with dipoles generated from dimethyl acetylenedicarboxylate and pyridine was found to proceed regioselectively affording spiro[pyrido[2,1-b][1,3]oxazine-2,3'-pyrroles] as diastereomeric mixtures which exist in rapid equilibrium in solution. It was established that this phenomenon of rapid epimerization is a characteristic of other similar spiropyrido[2,1-b][1,3]oxazines and even related spiroquinolizines, which was demonstrated by the investigation of related products of previously reported, and reproduced in this work, 1,4-dipolar cycloaddition reactions.
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Galeev A. R. et al. Cycloaddition of Huisgen 1,4-dipoles: Synthesis and rapid epimerization of functionalized spiropyrido[2,1-: B] [1,3]oxazine-pyrroles and related products // RSC Advances. 2022. Vol. 12. No. 1. pp. 578-587.
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Galeev A. R., Moroz I. A., Dmitriev M. V., Maslivets A. N. Cycloaddition of Huisgen 1,4-dipoles: Synthesis and rapid epimerization of functionalized spiropyrido[2,1-: B] [1,3]oxazine-pyrroles and related products // RSC Advances. 2022. Vol. 12. No. 1. pp. 578-587.
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TY - JOUR
DO - 10.1039/d1ra08384h
UR - https://xlink.rsc.org/?DOI=D1RA08384H
TI - Cycloaddition of Huisgen 1,4-dipoles: Synthesis and rapid epimerization of functionalized spiropyrido[2,1-: B] [1,3]oxazine-pyrroles and related products
T2 - RSC Advances
AU - Galeev, Andrew R
AU - Moroz, Ilya A
AU - Dmitriev, Maksim V
AU - Maslivets, Andrey N
PY - 2022
DA - 2022/01/01
PB - Royal Society of Chemistry (RSC)
SP - 578-587
IS - 1
VL - 12
PMID - 35424489
SN - 2046-2069
ER -
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@article{2022_Galeev,
author = {Andrew R Galeev and Ilya A Moroz and Maksim V Dmitriev and Andrey N Maslivets},
title = {Cycloaddition of Huisgen 1,4-dipoles: Synthesis and rapid epimerization of functionalized spiropyrido[2,1-: B] [1,3]oxazine-pyrroles and related products},
journal = {RSC Advances},
year = {2022},
volume = {12},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://xlink.rsc.org/?DOI=D1RA08384H},
number = {1},
pages = {578--587},
doi = {10.1039/d1ra08384h}
}
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MLA
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Galeev, Andrew R., et al. “Cycloaddition of Huisgen 1,4-dipoles: Synthesis and rapid epimerization of functionalized spiropyrido[2,1-: B] [1,3]oxazine-pyrroles and related products.” RSC Advances, vol. 12, no. 1, Jan. 2022, pp. 578-587. https://xlink.rsc.org/?DOI=D1RA08384H.