Three-Component [2+2+1] Gold(I)-Catalyzed Oxidative Generation of Fully Substituted 1,3-Oxazoles Involving Internal Alkynes

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4 Citations (Scopus)

Abstract

Three-component [2+2+1] gold(I)-catalyzed reaction of internal alkynes (alkynyl esters or -ketones), nitriles, and 2-chloropyridine N-oxide led to a wide range of fully substituted 1,3-oxazoles (32 examples; up to 92% isolated yields). Nitrile R 3 CN species, employed in the reaction as both reactants and solvents, comprise conventional nitriles (R 3 =Alk, Ar) and also push-pull systems such as cyanamides (R 3 =NH 2 and NAlk 2 ) and the thiocyanate (R 3 =SPr). The advantages of the developed method include mild reaction conditions, high functional-group tolerance, broad range of substituents R 1 /R 3 along with a possibility of easy modification of COR 2 or the amino group when R 1 =NH 2 . (Figure presented.).

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
DOIs
Publication statusPublished - 1 Jan 2019

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Oxazoles
Lead oxide
Nitriles
Alkynes
Ketones
Gold
Functional groups
Esters
Cyanamide

Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

@article{627e7be776cf49e99e5ca5c54f73f4b9,
title = "Three-Component [2+2+1] Gold(I)-Catalyzed Oxidative Generation of Fully Substituted 1,3-Oxazoles Involving Internal Alkynes",
abstract = "Three-component [2+2+1] gold(I)-catalyzed reaction of internal alkynes (alkynyl esters or -ketones), nitriles, and 2-chloropyridine N-oxide led to a wide range of fully substituted 1,3-oxazoles (32 examples; up to 92{\%} isolated yields). Nitrile R 3 CN species, employed in the reaction as both reactants and solvents, comprise conventional nitriles (R 3 =Alk, Ar) and also push-pull systems such as cyanamides (R 3 =NH 2 and NAlk 2 ) and the thiocyanate (R 3 =SPr). The advantages of the developed method include mild reaction conditions, high functional-group tolerance, broad range of substituents R 1 /R 3 along with a possibility of easy modification of COR 2 or the amino group when R 1 =NH 2 . (Figure presented.).",
keywords = "Heterocycles, Homogeneous catalysis, Oxidation, Gold catalysts, Synthetic methods",
author = "Dubovtsev, {Alexey Yu} and Dar'in, {Dmitry V.} and Kukushkin, {Vadim Yu}",
year = "2019",
month = "1",
day = "1",
doi = "10.1002/adsc.201900097",
language = "English",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-Blackwell",

}

TY - JOUR

T1 - Three-Component [2+2+1] Gold(I)-Catalyzed Oxidative Generation of Fully Substituted 1,3-Oxazoles Involving Internal Alkynes

AU - Dubovtsev, Alexey Yu

AU - Dar'in, Dmitry V.

AU - Kukushkin, Vadim Yu

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Three-component [2+2+1] gold(I)-catalyzed reaction of internal alkynes (alkynyl esters or -ketones), nitriles, and 2-chloropyridine N-oxide led to a wide range of fully substituted 1,3-oxazoles (32 examples; up to 92% isolated yields). Nitrile R 3 CN species, employed in the reaction as both reactants and solvents, comprise conventional nitriles (R 3 =Alk, Ar) and also push-pull systems such as cyanamides (R 3 =NH 2 and NAlk 2 ) and the thiocyanate (R 3 =SPr). The advantages of the developed method include mild reaction conditions, high functional-group tolerance, broad range of substituents R 1 /R 3 along with a possibility of easy modification of COR 2 or the amino group when R 1 =NH 2 . (Figure presented.).

AB - Three-component [2+2+1] gold(I)-catalyzed reaction of internal alkynes (alkynyl esters or -ketones), nitriles, and 2-chloropyridine N-oxide led to a wide range of fully substituted 1,3-oxazoles (32 examples; up to 92% isolated yields). Nitrile R 3 CN species, employed in the reaction as both reactants and solvents, comprise conventional nitriles (R 3 =Alk, Ar) and also push-pull systems such as cyanamides (R 3 =NH 2 and NAlk 2 ) and the thiocyanate (R 3 =SPr). The advantages of the developed method include mild reaction conditions, high functional-group tolerance, broad range of substituents R 1 /R 3 along with a possibility of easy modification of COR 2 or the amino group when R 1 =NH 2 . (Figure presented.).

KW - Heterocycles

KW - Homogeneous catalysis

KW - Oxidation, Gold catalysts

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=85064506007&partnerID=8YFLogxK

U2 - 10.1002/adsc.201900097

DO - 10.1002/adsc.201900097

M3 - Article

AN - SCOPUS:85064506007

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

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