32968-44-8Relevant academic research and scientific papers
A combinatorially convenient version of synthesis of 5-substituted oxazole-4-carboxylic acid ethyl esters
Tormyshev,Mikhalina,Rogozhnikova,Troitskaya,Trukhin
, p. 1031 - 1035 (2006)
Reaction of ethyl isocyanoacetic acid with sodium hydride in anhydrous benzene, followed by treatment with carboxylic acid chlorides or N-(acyloxy)pyrrolidine-2,5-diones, gives 5-substituted oxazole-4-carboxylic acid esters. The procedure is applicable to
Expanding the chemical space of sp 3-enriched 4,5-disubstituted oxazoles via synthesis of novel building blocks
Slobodyanyuk, Evgeniy Y.,Andriienko, Andrii A.,Vashchenko, Bohdan V.,Volochnyuk, Dmitriy M.,Ryabukhin, Sergey V.,Grygorenko, Oleksandr O.
, p. 421 - 434 (2019/06/20)
[Figure not available: see fulltext.] An efficient approach to the preparation of novel sp3-enriched 4,5-disubstituted oxazoles bearing a functional group at the C-4 position is described. The method commenced with synthesis of ethyl oxazole-4-carboxylates (13 examples, 63–99% yield), with subsequent function insertion to the heterocyclic core by late-stage functional group transformation. The LiBH4-mediated reduction of ethyl oxazole-4-carboxylates was the only method which could be optimized at multigram scale (up to 40 g), and its scope was demonstrated by preparation of 13 alcohols with (cyclo)alkyl, fluoroalkyl, or N-Boc-aminoalkyl moiety at the C-5 position (47–89% yield). The utility of these key intermediates was demonstrated by the preparation of chlorides (13 examples, 90–99% yield), azides (13 examples, 83–99% yield), amines (13 examples, 80–98% yield), and sulfonyl chlorides (4 examples, 68–97% yield) – advanced building blocks for synthetic and medicinal chemistry.
Synthesis of oxazoles by silver catalysed oxidative decarboxylation-cyclization of α-oxocarboxylates and isocyanides
Ma, Yiyang,Yan, Zhiyuan,Bian, Changliang,Li, Ke,Zhang, Xiaowen,Wang, Mengfan,Gao, Xinlong,Zhang, Heng,Lei, Aiwen
supporting information, p. 10524 - 10527 (2015/06/25)
A silver catalysed synthesis of oxazoles by the oxidative decarboxylation-cyclization of α-oxocarboxylates and isocyanides was developed. This method provided a novel strategy to construct oxazole rings compared to traditional methods. Mechanistic investigations such as operando IR, EPR and radical inhibition experiments were carefully done and confirmed the acyl cation and Ag(ii) as the intermediates in this transformation, and the involvement of a radical decarboxylative process.
Mechanism selection for regiocontrol in base-assisted, palladium-catalysed direct C-H coupling with halides: First approach for oxazole- and thiazole-4-carboxylates
Théveau, Laure,Verrier, Cécile,Lassalas, Pierrik,Martin, Thibaut,Dupas, Georges,Querolle, Olivier,Van Hijfte, Luc,Marsais, Francis,Hoarau, Christophe
supporting information; experimental part, p. 14450 - 14463 (2012/01/15)
Both base-assisted non-concerted metallation-deprotonation (nCMD) and concerted metallation-deprotonation (CMD) have been identified as two potent operating mechanisms in palladium-catalysed direct C-H coupling of oxazole and thiazole-4-carboxylate esters
Lipophilic 5,6,7,8-tetrahydropterin substrates for phenylalanine hydroxylase (monkey brain), tryptophan hydroxylase (rat brain) and tyrosine hydroxylase (rat brain)
Armarego, Wilfred L. F.,Taguchi, Hiroyasu,Cotton, Richard G. H.,Battiston, Sandra,Leong, Lillian
, p. 283 - 292 (2007/10/02)
A high yielding unambiguous synthesis of (+/-)-6-alkyl-5,6,7,8-tetrahydropterin 5a-f hydrochlorides starting from ethyl α-isocyanoacetate 1 and the respective alkanoic anhydrides or alkanoyl chlorides in four steps is described.All the six pterins 5a-f that have been synthesised are substrates for mammalian phenylalanine, tryptophan and tyrosine hydroxylases and their activities have been compared with those of natural 6R-tetrahydrobiopterin under similar conditions.The data allowed the choice of 6-n-propyl-5,6,7,8-tetrahydropterin 5c for further studies as a candidate for tetrahydrobiopterin drug therapy.Keywords: (+/-)-6-alkyltetrahydropterinsydroxylase / tryptophan hydroxylase / tyrosine hydroxylase
