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Three-Component [2+2+1] Gold(I)-Catalyzed Oxidative Generation of Fully Substituted 1,3-Oxazoles Involving Internal Alkynes. / Dubovtsev, Alexey Yu; Dar'in, Dmitry V.; Kukushkin, Vadim Yu.

In: Advanced Synthesis and Catalysis, Vol. 361, No. 12, 18.06.2019, p. 2926-2935.

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

Harvard

Dubovtsev, AY, Dar'in, DV & Kukushkin, VY 2019, 'Three-Component [2+2+1] Gold(I)-Catalyzed Oxidative Generation of Fully Substituted 1,3-Oxazoles Involving Internal Alkynes', Advanced Synthesis and Catalysis, vol. 361, no. 12, pp. 2926-2935. https://doi.org/10.1002/adsc.201900097

APA

Dubovtsev, A. Y., Dar'in, D. V., & Kukushkin, V. Y. (2019). Three-Component [2+2+1] Gold(I)-Catalyzed Oxidative Generation of Fully Substituted 1,3-Oxazoles Involving Internal Alkynes. Advanced Synthesis and Catalysis, 361(12), 2926-2935. https://doi.org/10.1002/adsc.201900097

Vancouver

Dubovtsev AY, Dar'in DV, Kukushkin VY. Three-Component [2+2+1] Gold(I)-Catalyzed Oxidative Generation of Fully Substituted 1,3-Oxazoles Involving Internal Alkynes. Advanced Synthesis and Catalysis. 2019 Jun 18;361(12):2926-2935. https://doi.org/10.1002/adsc.201900097

Author

Dubovtsev, Alexey Yu ; Dar'in, Dmitry V. ; Kukushkin, Vadim Yu. / Three-Component [2+2+1] Gold(I)-Catalyzed Oxidative Generation of Fully Substituted 1,3-Oxazoles Involving Internal Alkynes. In: Advanced Synthesis and Catalysis. 2019 ; Vol. 361, No. 12. pp. 2926-2935.

BibTeX

@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, ROOM-TEMPERATURE, CATALYSIS, COMPLEXES, TERMINAL ALKYNES, Gold catalysts, HYDRATION, REGIOSELECTIVE SYNTHESIS, BIOLOGICAL EVALUATION, Oxidation, OXO GOLD CARBENES, 2,5-DISUBSTITUTED OXAZOLES, DERIVATIVES",
author = "Dubovtsev, {Alexey Yu} and Dar'in, {Dmitry V.} and Kukushkin, {Vadim Yu}",
year = "2019",
month = jun,
day = "18",
doi = "10.1002/adsc.201900097",
language = "English",
volume = "361",
pages = "2926--2935",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-Blackwell",
number = "12",

}

RIS

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 - 2019/6/18

Y1 - 2019/6/18

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

KW - ROOM-TEMPERATURE

KW - CATALYSIS

KW - COMPLEXES

KW - TERMINAL ALKYNES

KW - Gold catalysts

KW - HYDRATION

KW - REGIOSELECTIVE SYNTHESIS

KW - BIOLOGICAL EVALUATION

KW - Oxidation

KW - OXO GOLD CARBENES

KW - 2,5-DISUBSTITUTED OXAZOLES

KW - DERIVATIVES

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

UR - http://www.mendeley.com/research/threecomponent-221-goldicatalyzed-oxidative-generation-fully-substituted-13oxazoles-involving-intern

U2 - 10.1002/adsc.201900097

DO - 10.1002/adsc.201900097

M3 - Article

AN - SCOPUS:85064506007

VL - 361

SP - 2926

EP - 2935

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 12

ER -

ID: 41786828