126773-83-9Relevant academic research and scientific papers
Preparation of 2,5-disubstituted oxazoles from N-propargylamides.
Arcadi,Cacchi,Cascia,Fabrizi,Marinelli
, p. 2501 - 2504 (2001)
[reaction: see text] 2,5-Disubstituted oxazoles have been prepared through the reaction of N-propargylamides with aryl iodides in the presence of Pd(2)(dba)(3), tri(2-furyl)phosphine, and NaO(t)()Bu. The reaction appears to proceed through a palladium-catalyzed coupling step followed by the in situ cyclization of the resultant coupling product.
Base-Promoted Cycloisomerization for the Synthesis of Oxazoles and Imidazoles
Zhang, Lidan,Xiao, Ke,Qiao, Yan,Li, Xin,Song, Chuanjun,Chang, Junbiao
, p. 6913 - 6918 (2018/12/05)
Treatment of propargylamides or propargylamidines with cesium carbonate in DMSO results in the formation of the corresponding oxazoles or imidazoles in good yields. A large variety of substrates with various functional groups are tolerated. DFT study on a model substrate reveals that the reactions proceed via a sequence involving allene formation, intramolecular cyclization, and double-bond isomerization.
Synthesis of substituted oxazoles from N-benzyl propargyl amines and acid chlorides
Wachenfeldt, Henrik V.,Paulsen, Filip,Sundin, Anders,Strand, Daniel
, p. 4578 - 4585 (2013/07/26)
The reaction between N-benzylpropargylamines and acid chlorides at elevated temperatures provides efficient, direct access to a variety of di- and tri-substituted oxazoles. The versatility of this reaction is explored and 21 examples are demonstrated. The usefulness of the methodology is showcased through the short and efficient formal syntheses of medicinally relevant drugs aleglitazar and romazarit. The reaction between N-benzylpropargylamines and acid chlorides at elevated temperatures gives oxazoles in up to 99 % yield. Twenty-one examples are demonstrated varying the substitution at all positions of the heterocycle. Copyright
Catalytic three-component domino reaction for the preparation of trisubstituted oxazoles
Wachenfeldt, Henrik V.,R?se, Philipp,Paulsen, Filip,Loganathan, Nagarajan,Strand, Daniel
supporting information, p. 7982 - 7988 (2013/07/25)
Multicomponent reactions are attractive for assembling functionalized heterocyclic compounds. To this end, an efficient gold-catalyzed three-component domino reaction to form oxazoles directly from imines, alkynes, and acid chlorides is presented. The reaction proceeds in a single synthetic step by using a gold(III)-N,N'-ethylenebis(salicylimine) (salen) catalyst to give trisubstituted oxazoles in up to 96 % yield. The substrate scope, a mechanistic study exploring the role of the gold catalyst, and the synthetic applications of the oxazole products are discussed. Copyright
Synthesis of oxazoles through Pd-catalyzed cycloisomerization-allylation of N-propargylamides with allyl carbonates
Saito, Akio,Iimura, Koichi,Hanzawa, Yuji
scheme or table, p. 1471 - 1474 (2010/04/29)
In the presence of Pd2(dba)3-Cy3P catalyst, IPr·HCl salt [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], and Cs2CO3, N-propargylamides react with allyl carbonates to give 2,5-disubstituted o
Palladium-catalyzed benzylation of heterocyclic aromatic compounds
Lapointe, David,Fagnou, Keith
supporting information; experimental part, p. 4160 - 4163 (2009/12/07)
Broadly applicable palladium-catalyzed heteroarene benzylation reactions are described with a focus on the most challenging heterocyclic classes under traditional benzylation techniques such as sulfur-containing heterocycles and those bearing functional groups that would be incompatible with reactions requiring Lewis acids and/or strong bases.
Synthesis of 2-Aryl- and 5-Alkyl-2-aryloxazoles from 2-Aryl-5-bromooxazoles
Kashima, Choji,Arao, Hideki
, p. 873 - 874 (2007/10/02)
2-Aryloxazoles, their 5-deuterio derivatives, and 5-alkyl-2-aryloxazoles are prepared in good yields from 2-aryl-5-bromooxazoles via halogen/metal exchange with butyllithium followed by treatment with water, methanol-O-d, or alkyl halides, respectively.
