Organic Letters, volume 20, issue 24, pages 8039-8042
Oxidative Cyclization Protocol for the Preparation of Energetic 3-Amino-5-R-1,2,4-oxadiazoles
1
Department of Chemistry, University of Idaho, Moscow, Idaho 83844-2343, United States
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2
Naval Research Laboratory, 4555 Overlook Avenue, Washington, D.C. 20375, United States
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Publication type: Journal Article
Publication date: 2018-12-10
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
An efficient method has been developed for the synthesis of energetic 3-amino-5- R-1,2,4-oxadiazoles via iodobenzene diacetate (IBD)-mediated oxidative cyclization in high yields at ambient temperature. Compound 1c has a graphite-like structure, which has seldom been reported in bicyclic compounds. The reaction of 3-amino-5- R-1,2,4-oxadiazole derivatives with hydrazine monohydrate in THF gives products that are a function of the substituent. Energetic performance calculations show detonation properties superior to TNT with concomitant lower impact and friction sensitivities.
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Tang, Y. et al. Oxidative Cyclization Protocol for the Preparation of Energetic 3-Amino-5-R-1,2,4-oxadiazoles // Organic Letters. 2018. Vol. 20. No. 24. pp. 8039-8042.
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Tang, Y., Imler G. H., Parrish D. A., Shreeve J. M. Oxidative Cyclization Protocol for the Preparation of Energetic 3-Amino-5-R-1,2,4-oxadiazoles // Organic Letters. 2018. Vol. 20. No. 24. pp. 8039-8042.
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TY - JOUR
DO - 10.1021/acs.orglett.8b03639
UR - https://doi.org/10.1021/acs.orglett.8b03639
TI - Oxidative Cyclization Protocol for the Preparation of Energetic 3-Amino-5-R-1,2,4-oxadiazoles
T2 - Organic Letters
AU - Parrish, Damon A.
AU - Tang,, Yongxing
AU - Shreeve, Jean'ne M.
AU - Imler, Gregory H
PY - 2018
DA - 2018/12/10 00:00:00
PB - American Chemical Society (ACS)
SP - 8039-8042
IS - 24
VL - 20
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2018_Tang,,
author = {Damon A. Parrish and Yongxing Tang, and Jean'ne M. Shreeve and Gregory H Imler},
title = {Oxidative Cyclization Protocol for the Preparation of Energetic 3-Amino-5-R-1,2,4-oxadiazoles},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.orglett.8b03639},
number = {24},
pages = {8039--8042},
doi = {10.1021/acs.orglett.8b03639}
}
Cite this
MLA
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Tang,, Yongxing, et al. “Oxidative Cyclization Protocol for the Preparation of Energetic 3-Amino-5-R-1,2,4-oxadiazoles.” Organic Letters, vol. 20, no. 24, Dec. 2018, pp. 8039-8042. https://doi.org/10.1021/acs.orglett.8b03639.
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