Synthesis of 1,2,4-Oxadiazoles by Tandem Reaction of Nitroalkenes with Arenes and Nitriles in the Superacid TfOH

Research output

Abstract

The tandem reaction of nitroalkenes with arenes and nitriles in the superacid CF3SO3H (TfOH) results in the formation of 1,2,4-oxadiazole derivatives in yields up to 96%. This reaction proceeds via the consequent interaction of arenes and nitriles, as nucleophiles, with intermediate cationic species derived by the protonation of nitroalkenes in TfOH. This is novel and general synthesis of 1,2,4-oxadiazoles, which are very important compounds for medicinal chemistry.

Original languageEnglish
Pages (from-to)7495-7500
Number of pages6
JournalJournal of Organic Chemistry
Volume84
Issue number11
DOIs
Publication statusPublished - 7 Jun 2019

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Oxadiazoles
Nitriles
Nucleophiles
Protonation
Derivatives
Pharmaceutical Chemistry

Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Synthesis of 1,2,4-Oxadiazoles by Tandem Reaction of Nitroalkenes with Arenes and Nitriles in the Superacid TfOH",
abstract = "The tandem reaction of nitroalkenes with arenes and nitriles in the superacid CF3SO3H (TfOH) results in the formation of 1,2,4-oxadiazole derivatives in yields up to 96{\%}. This reaction proceeds via the consequent interaction of arenes and nitriles, as nucleophiles, with intermediate cationic species derived by the protonation of nitroalkenes in TfOH. This is novel and general synthesis of 1,2,4-oxadiazoles, which are very important compounds for medicinal chemistry.",
author = "Golushko, {Andrei A.} and Khoroshilova, {Olesya V.} and Vasilyev, {Aleksander V.}",
year = "2019",
month = "6",
day = "7",
doi = "10.1021/acs.joc.9b00812",
language = "English",
volume = "84",
pages = "7495--7500",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "11",

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TY - JOUR

T1 - Synthesis of 1,2,4-Oxadiazoles by Tandem Reaction of Nitroalkenes with Arenes and Nitriles in the Superacid TfOH

AU - Golushko, Andrei A.

AU - Khoroshilova, Olesya V.

AU - Vasilyev, Aleksander V.

PY - 2019/6/7

Y1 - 2019/6/7

N2 - The tandem reaction of nitroalkenes with arenes and nitriles in the superacid CF3SO3H (TfOH) results in the formation of 1,2,4-oxadiazole derivatives in yields up to 96%. This reaction proceeds via the consequent interaction of arenes and nitriles, as nucleophiles, with intermediate cationic species derived by the protonation of nitroalkenes in TfOH. This is novel and general synthesis of 1,2,4-oxadiazoles, which are very important compounds for medicinal chemistry.

AB - The tandem reaction of nitroalkenes with arenes and nitriles in the superacid CF3SO3H (TfOH) results in the formation of 1,2,4-oxadiazole derivatives in yields up to 96%. This reaction proceeds via the consequent interaction of arenes and nitriles, as nucleophiles, with intermediate cationic species derived by the protonation of nitroalkenes in TfOH. This is novel and general synthesis of 1,2,4-oxadiazoles, which are very important compounds for medicinal chemistry.

UR - http://www.scopus.com/inward/record.url?scp=85066400452&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.9b00812

DO - 10.1021/acs.joc.9b00812

M3 - Article

C2 - 31117566

AN - SCOPUS:85066400452

VL - 84

SP - 7495

EP - 7500

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 11

ER -