Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions

Standard

Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions. / Puzanov, Andrey I.; Ryabukhin, Dmitry S.; Zalivatskaya, Anna S.; Zakusilo, Dmitriy N.; Mikson, Darya S.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.

в: Beilstein Journal of Organic Chemistry, Том 17, 15.09.2021, стр. 2417-2424.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Author

Puzanov, Andrey I. ; Ryabukhin, Dmitry S. ; Zalivatskaya, Anna S. ; Zakusilo, Dmitriy N. ; Mikson, Darya S. ; Boyarskaya, Irina A. ; Vasilyev, Aleksander V. / Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions. в: Beilstein Journal of Organic Chemistry. 2021 ; Том 17. стр. 2417-2424.

BibTeX

@article{fb8daa91775542c6992a2f795bd93127,

title = "Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions",

abstract = "Acetylene derivatives of 1,2,4-oxadiazoles, i.e., 5-(2-arylethynyl)-3-aryl-1,2,4-oxadiazoles, have been obtained, for the first time reported, from 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles by their bromination at the carbon-carbon double bond followed by di-dehydrobromination with NaNH2 in liquid NH3. The reaction of the acetylenyl-1,2,4-oxadiazoles with arenes in neat triflic acid TfOH (CF3SO3H) at room temperature for 1 h resulted in the formation of E/Z-5-(2,2-diarylethenyl)-3-aryl-1,2,4-oxadiazoles as products of regioselective hydroarylation of the acetylene bond. The addition of TfOH to the acetylene bond of these oxadiazoles quantitatively resulted in E/Z-vinyl triflates. The reactions of the cationic intermediates have been studied by DFT calculations and the reaction mechanisms are discussed.",

keywords = "Acetylene-oxadiazoles, Friedel-Crafts reaction, Hydroarylation, Superelectrophilic activation, Triflic acid, 1,2,4-OXADIAZOLES, superelectrophilic activation, triflic acid, acetylene-oxadiazoles, BIOLOGICAL EVALUATION, CHEMISTRY, hydroarylation, DERIVATIVES",

author = "Puzanov, {Andrey I.} and Ryabukhin, {Dmitry S.} and Zalivatskaya, {Anna S.} and Zakusilo, {Dmitriy N.} and Mikson, {Darya S.} and Boyarskaya, {Irina A.} and Vasilyev, {Aleksander V.}",

note = "Publisher Copyright: {\textcopyright} 2021 Puzanov et al.; licensee Beilstein-Institut. License and terms: see end of document.",

year = "2021",

month = sep,

day = "15",

doi = "10.3762/bjoc.17.158",

language = "English",

volume = "17",

pages = "2417--2424",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

RIS

TY - JOUR

T1 - Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions

AU - Puzanov, Andrey I.

AU - Ryabukhin, Dmitry S.

AU - Zalivatskaya, Anna S.

AU - Zakusilo, Dmitriy N.

AU - Mikson, Darya S.

AU - Boyarskaya, Irina A.

AU - Vasilyev, Aleksander V.

PY - 2021/9/15

Y1 - 2021/9/15

N2 - Acetylene derivatives of 1,2,4-oxadiazoles, i.e., 5-(2-arylethynyl)-3-aryl-1,2,4-oxadiazoles, have been obtained, for the first time reported, from 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles by their bromination at the carbon-carbon double bond followed by di-dehydrobromination with NaNH2 in liquid NH3. The reaction of the acetylenyl-1,2,4-oxadiazoles with arenes in neat triflic acid TfOH (CF3SO3H) at room temperature for 1 h resulted in the formation of E/Z-5-(2,2-diarylethenyl)-3-aryl-1,2,4-oxadiazoles as products of regioselective hydroarylation of the acetylene bond. The addition of TfOH to the acetylene bond of these oxadiazoles quantitatively resulted in E/Z-vinyl triflates. The reactions of the cationic intermediates have been studied by DFT calculations and the reaction mechanisms are discussed.

AB - Acetylene derivatives of 1,2,4-oxadiazoles, i.e., 5-(2-arylethynyl)-3-aryl-1,2,4-oxadiazoles, have been obtained, for the first time reported, from 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles by their bromination at the carbon-carbon double bond followed by di-dehydrobromination with NaNH2 in liquid NH3. The reaction of the acetylenyl-1,2,4-oxadiazoles with arenes in neat triflic acid TfOH (CF3SO3H) at room temperature for 1 h resulted in the formation of E/Z-5-(2,2-diarylethenyl)-3-aryl-1,2,4-oxadiazoles as products of regioselective hydroarylation of the acetylene bond. The addition of TfOH to the acetylene bond of these oxadiazoles quantitatively resulted in E/Z-vinyl triflates. The reactions of the cationic intermediates have been studied by DFT calculations and the reaction mechanisms are discussed.

KW - Acetylene-oxadiazoles

KW - Friedel-Crafts reaction

KW - Hydroarylation

KW - Superelectrophilic activation

KW - Triflic acid

KW - 1,2,4-OXADIAZOLES

KW - superelectrophilic activation

KW - triflic acid

KW - acetylene-oxadiazoles

KW - BIOLOGICAL EVALUATION

KW - CHEMISTRY

KW - hydroarylation

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85115187771&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/2ad12fc5-4ef9-36c1-8d29-c195e844c4e6/

U2 - 10.3762/bjoc.17.158

DO - 10.3762/bjoc.17.158

M3 - Article

C2 - 34621403

AN - SCOPUS:85115187771

VL - 17

SP - 2417

EP - 2424

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

ID: 86657418