Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes
4
Marshall School, Duluth, Minnesota 55811, United States
|
Publication type: Journal Article
Publication date: 2017-07-31
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
28730819
Organic Chemistry
Abstract
An efficient cycloaddition of heterocyclic alkenes with nitrile oxides generated in situ from the corresponding aldoximes using organohypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (Koser's reagent), has been developed. The oxidative cyclization of various aldoximes with 1-propene-1,3-sultone affords the respective isoxazoline-ring-fused heterobicyclic products in moderate to good yields. Furthermore, the reaction of aldoxime with a cyclic phospholene-oxide under similar conditions produces the corresponding heterobicyclic phospholene oxides in moderate yields. The structures of bicyclic phospholene oxide and two sultones were established by single-crystal X-ray crystallography.
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GOST
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YOSHIMURA A. et al. Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes // Journal of Organic Chemistry. 2017. Vol. 82. No. 22. pp. 11742-11751.
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YOSHIMURA A., Nguyen K. C., Rohde G., Postnikov P. S., S. Yusubov M., Zhdankin V. V. Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes // Journal of Organic Chemistry. 2017. Vol. 82. No. 22. pp. 11742-11751.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.7b01462
UR - https://doi.org/10.1021/acs.joc.7b01462
TI - Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes
T2 - Journal of Organic Chemistry
AU - YOSHIMURA, Akira
AU - Nguyen, Khiem C
AU - Rohde, Gregory
AU - Postnikov, Pavel S.
AU - S. Yusubov, Mekhman
AU - Zhdankin, Viktor V.
PY - 2017
DA - 2017/07/31
PB - American Chemical Society (ACS)
SP - 11742-11751
IS - 22
VL - 82
PMID - 28730819
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2017_YOSHIMURA,
author = {Akira YOSHIMURA and Khiem C Nguyen and Gregory Rohde and Pavel S. Postnikov and Mekhman S. Yusubov and Viktor V. Zhdankin},
title = {Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.joc.7b01462},
number = {22},
pages = {11742--11751},
doi = {10.1021/acs.joc.7b01462}
}
Cite this
MLA
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YOSHIMURA, Akira, et al. “Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes.” Journal of Organic Chemistry, vol. 82, no. 22, Jul. 2017, pp. 11742-11751. https://doi.org/10.1021/acs.joc.7b01462.