Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles

Результат исследований: Научные публикации в периодических изданияхстатья

3 Цитирования (Scopus)

Выдержка

Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by α-picoline N-oxide in the presence of Ph 3 PAuNТf 2 (5 mol-%). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 °C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space.

Язык оригиналаанглийский
Страницы (с-по)1856-1864
Число страниц9
ЖурналEuropean Journal of Organic Chemistry
Том2019
Номер выпуска8
DOI
СостояниеОпубликовано - 28 фев 2019

Отпечаток

Alkynes
alkynes
Gold
Picolines
Imidazoles
gold
Pyrazines
quinoxalines
Quinoxalines
Oxidation
oxidation
chlorobenzenes
pyrazines
Dione
synthesis
imidazoles
Oxides
reagents
oxides
rings

Предметные области Scopus

  • Физическая и теоретическая химия
  • Органическая химия

Цитировать

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title = "Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles",
abstract = "Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by α-picoline N-oxide in the presence of Ph 3 PAuNТf 2 (5 mol-{\%}). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 °C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space.",
keywords = "Gold, Heterocycles, Homogeneous catalysis, Oxidation, Synthetic methods, COMPLEXES, EFFICIENT SYNTHESIS, TERMINAL ALKYNES, CARBOXYLESTERASES, HIGHLY EFFICIENT, QUINOXALINE, INHIBITION, RING, CYCLOISOMERIZATION, DERIVATIVES",
author = "Dubovtsev, {Alexey Yu} and Dar'in, {Dmitry V.} and Mikhail Krasavin and Kukushkin, {Vadim Yu}",
year = "2019",
month = "2",
day = "28",
doi = "10.1002/ejoc.201900108",
language = "English",
volume = "2019",
pages = "1856--1864",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "8",

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Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles. / Dubovtsev, Alexey Yu; Dar'in, Dmitry V.; Krasavin, Mikhail; Kukushkin, Vadim Yu.

В: European Journal of Organic Chemistry, Том 2019, № 8, 28.02.2019, стр. 1856-1864.

Результат исследований: Научные публикации в периодических изданияхстатья

TY - JOUR

T1 - Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles

AU - Dubovtsev, Alexey Yu

AU - Dar'in, Dmitry V.

AU - Krasavin, Mikhail

AU - Kukushkin, Vadim Yu

PY - 2019/2/28

Y1 - 2019/2/28

N2 - Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by α-picoline N-oxide in the presence of Ph 3 PAuNТf 2 (5 mol-%). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 °C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space.

AB - Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by α-picoline N-oxide in the presence of Ph 3 PAuNТf 2 (5 mol-%). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 °C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space.

KW - Gold

KW - Heterocycles

KW - Homogeneous catalysis

KW - Oxidation

KW - Synthetic methods

KW - COMPLEXES

KW - EFFICIENT SYNTHESIS

KW - TERMINAL ALKYNES

KW - CARBOXYLESTERASES

KW - HIGHLY EFFICIENT

KW - QUINOXALINE

KW - INHIBITION

KW - RING

KW - CYCLOISOMERIZATION

KW - DERIVATIVES

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UR - http://www.mendeley.com/research/goldcatalyzed-oxidation-internal-alkynes-benzils-application-onepot-synthesis-five-six-sevenmembered

U2 - 10.1002/ejoc.201900108

DO - 10.1002/ejoc.201900108

M3 - Article

AN - SCOPUS:85061434062

VL - 2019

SP - 1856

EP - 1864

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 8

ER -