2-(1,2,4-Oxadiazol-5-yl)anilines Based on Amidoximes and Isatoic Anhydrides: Synthesis and Structure Features

Standard

2-(1,2,4-Oxadiazol-5-yl)anilines Based on Amidoximes and Isatoic Anhydrides: Synthesis and Structure Features. / Тарасенко, Марина; Котлярова, В.; Байков, Сергей Валентинович; Шетнев, Антон.

In: Russian Journal of General Chemistry, Vol. 91, No. 5, 05.2021, p. 768–778.

Research output: Contribution to journal › Article › peer-review

Author

Тарасенко, Марина ; Котлярова, В. ; Байков, Сергей Валентинович ; Шетнев, Антон. / 2-(1,2,4-Oxadiazol-5-yl)anilines Based on Amidoximes and Isatoic Anhydrides: Synthesis and Structure Features. In: Russian Journal of General Chemistry. 2021 ; Vol. 91, No. 5. pp. 768–778.

BibTeX

@article{c667c440b6004401b8f4b2f63cefe700,

title = "2-(1,2,4-Oxadiazol-5-yl)anilines Based on Amidoximes and Isatoic Anhydrides: Synthesis and Structure Features",

abstract = "Abstract: An efficient one-pot method was developed for the synthesis of 2-(1,2,4-oxadiazol-5-yl)anilines via the reaction of amidoximes with isatoic anhydrides in a NaOH–DMSO medium at ambient temperature. The method allows to obtain structurally diverse substituted anilines bearing the 1,2,4-oxadiazole motif in moderate to excellent yields without the utilization of protective groups. The reaction scope includes aryl, hetaryl, and cycloalkyl amidoxime and isatoic anhydrides with different substituents in the aromatic ring as well as at the amide N atom. Structures of two anilines were studied by single crystal X-ray diffraction method and intramolecular hydrogen bonding between N atom of oxadiazole moiety and NH 2 group was revealed. ",

keywords = "amidoximes, amines, base catalysis, heterocycles, ANTIMYCOBACTERIAL ACTIVITY, DESIGN, ONE-POT SYNTHESIS, OPICAPONE, DISCOVERY, BIPOLAR HOST MATERIALS, 3,5-DISUBSTITUTED 1,2,4-OXADIAZOLES, SELECTIVE INHIBITORS, DERIVATIVES, CYCLIZATION",

author = "Марина Тарасенко and В. Котлярова and Байков, {Сергей Валентинович} and Антон Шетнев",

note = "Publisher Copyright: {\textcopyright} 2021, Pleiades Publishing, Ltd.",

year = "2021",

month = may,

doi = "10.1134/S1070363221050030",

language = "English",

volume = "91",

pages = "768–778",

journal = "Russian Journal of General Chemistry",

issn = "1070-3632",

publisher = "МАИК {"}Наука/Интерпериодика{"}",

number = "5",

}

RIS

TY - JOUR

T1 - 2-(1,2,4-Oxadiazol-5-yl)anilines Based on Amidoximes and Isatoic Anhydrides: Synthesis and Structure Features

AU - Тарасенко, Марина

AU - Котлярова, В.

AU - Байков, Сергей Валентинович

AU - Шетнев, Антон

PY - 2021/5

Y1 - 2021/5

N2 - Abstract: An efficient one-pot method was developed for the synthesis of 2-(1,2,4-oxadiazol-5-yl)anilines via the reaction of amidoximes with isatoic anhydrides in a NaOH–DMSO medium at ambient temperature. The method allows to obtain structurally diverse substituted anilines bearing the 1,2,4-oxadiazole motif in moderate to excellent yields without the utilization of protective groups. The reaction scope includes aryl, hetaryl, and cycloalkyl amidoxime and isatoic anhydrides with different substituents in the aromatic ring as well as at the amide N atom. Structures of two anilines were studied by single crystal X-ray diffraction method and intramolecular hydrogen bonding between N atom of oxadiazole moiety and NH 2 group was revealed.

AB - Abstract: An efficient one-pot method was developed for the synthesis of 2-(1,2,4-oxadiazol-5-yl)anilines via the reaction of amidoximes with isatoic anhydrides in a NaOH–DMSO medium at ambient temperature. The method allows to obtain structurally diverse substituted anilines bearing the 1,2,4-oxadiazole motif in moderate to excellent yields without the utilization of protective groups. The reaction scope includes aryl, hetaryl, and cycloalkyl amidoxime and isatoic anhydrides with different substituents in the aromatic ring as well as at the amide N atom. Structures of two anilines were studied by single crystal X-ray diffraction method and intramolecular hydrogen bonding between N atom of oxadiazole moiety and NH 2 group was revealed.

KW - amidoximes

KW - amines

KW - base catalysis

KW - heterocycles

KW - ANTIMYCOBACTERIAL ACTIVITY

KW - DESIGN

KW - ONE-POT SYNTHESIS

KW - OPICAPONE

KW - DISCOVERY

KW - BIPOLAR HOST MATERIALS

KW - 3,5-DISUBSTITUTED 1,2,4-OXADIAZOLES

KW - SELECTIVE INHIBITORS

KW - DERIVATIVES

KW - CYCLIZATION

UR - http://www.scopus.com/inward/record.url?scp=85108343892&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/4b5a1c03-fec1-319c-9885-9bc8f14eaddb/

U2 - 10.1134/S1070363221050030

DO - 10.1134/S1070363221050030

M3 - Article

VL - 91

SP - 768

EP - 778

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

SN - 1070-3632

IS - 5

ER -

ID: 78042605