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

Dubovtsev Alexey Yu. | Zendy; Dar'in Dmitry V. | Zendy; Kukushkin Vadim Yu. | Zendy

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

Author(s) -

Dubovtsev Alexey Yu.,

Dar'in Dmitry V.,

Kukushkin Vadim Yu.

Publication year - 2019

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201900097

Subject(s) - chemistry , nitrile , catalysis , medicinal chemistry , functional group , combinatorial chemistry , thiocyanate , reaction conditions , oxide , oxidative phosphorylation , component (thermodynamics) , organic chemistry , polymer , physics , thermodynamics , biochemistry

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 .

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