Organic Letters

, том 20 , издание 24 , страницы 8039-8042

Oxidative Cyclization Protocol for the Preparation of Energetic 3-Amino-5-R-1,2,4-oxadiazoles

Тип публикации: Journal Article

Дата публикации: 2018-12-10

American Chemical Society (ACS)

Organic Letters

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SJR: 1.235

CiteScore: 8.7

Impact factor: 5

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.8b03639

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PubMed ID: 30525670

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Краткое описание

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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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 - Tang,, Yongxing

AU - Imler, Gregory H

AU - Parrish, Damon A.

AU - Shreeve, Jean'ne M.

PY - 2018

DA - 2018/12/10

PB - American Chemical Society (ACS)

SP - 8039-8042

IS - 24

VL - 20

PMID - 30525670

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2018_Tang,,

author = {Yongxing Tang, and Gregory H Imler and Damon A. Parrish and Jean'ne M. Shreeve},

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}

}

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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.