3988-65-6Relevant academic research and scientific papers
Method of coupling, and the coupling method using the aromatic group-substituted heterocyclic compound
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Paragraph 0292-0297; 0299, (2020/09/17)
Provided is an easy method (coupling method) capable of easily synthesizing a compound group in which aromatic molecules and aromatic molecules are coupled, a compound group in which aromatic molecules and alkene molecules are coupled, and the like without producing halogen waste and without the need to use scarce and expensive palladium. A compound (A) shown by general formula (A): Ar-H and a compound (B1) shown by general formula (B1): RaOCO-Ar', a compound (B2) shown by general formula (B2): RbCH=C(Ar")2, or a compound (B3) shown by general formula (B3): RcOCOCH=C(Ar")2 are reacted in the presence of a nickel compound.
One-pot conversion of amino acids into 2,5-disubstituted oxazoles: No metals needed
Romero-Estudillo, Ivan,Batchu, Venkateswara Rao,Boto, Alicia
supporting information, p. 3742 - 3748 (2015/01/16)
2,5-Disubstituted oxazoles with a variety of alkyl and aryl groups are efficiently formed from N-acylamino acids, by a one-pot radical decarboxylation- oxidation-enolization and iodine-promoted cyclization process. Remarkably, the reaction takes place under mild conditions, and no metal catalysis is needed. The process can be useful for the direct modification of small peptides.
C-H alkenylation of azoles with enols and esters by nickel catalysis
Meng, Lingkui,Kamada, Yuko,Muto, Kei,Yamaguchi, Junichiro,Itami, Kenichiro
, p. 10048 - 10051 (2013/10/01)
Rather u(Ni)que: Two new C-H alkenylation reactions, that is C-H/Ci£O alkenylation and decarbonylative C-H alkenylation, of azoles are uniquely catalyzed by Ni/dcype. These azole alkenylation reactions are successfully applied to the convergent formal synthesis of siphonazoleB.
Thermal transformations of alk-1-enyl-N-phthalimidoaziridines
Kuznetsov,Voronin
, p. 83 - 94 (2013/03/29)
Thermolysis of alk-1-enyl-N-phthalimidoaziridines leads to products of 1,5-electrocyclization of intermediate azomethine ylides with participation of C=C bonds. If acyl or alkoxycarbonyl substituent is present in the aziridine ring, the C=O bond is also i
Room temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization
Cheung, Chi Wai,Buchwald, Stephen L.
, p. 7526 - 7537 (2012/10/30)
A copper(II)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.
Copper(ii)-mediated oxidative cyclization of enamides to oxazoles
Wendlandt, Alison E.,Stahl, Shannon S.
supporting information; experimental part, p. 3866 - 3870 (2012/06/04)
The copper(ii)-mediated oxidative cyclization of enamides to oxazoles is reported. A range of 2,5-disubstituted oxazoles were prepared in moderate to good yields in two steps from simple amide and alkyne precursors.
Microwave-assisted Pd/Cu-catalyzed C-8 direct alkenylation of purines and related azoles: An alternative access to 6,8,9-trisubstituted purines
Vabre, Roxane,Chevot, Franciane,Legraverend, Michel,Piguel, Sandrine
experimental part, p. 9542 - 9547 (2011/12/22)
An efficient microwave-assisted palladium/copper comediated C-8 direct alkenylation of purines with styryl bromides has been developed. The method is regioselective, functional group tolerant, rapid, and compatible with other related azoles. Combined with
Simple and efficient preparation of 2,5-disubstituted oxazoles via a metal-free-catalyzed cascade cyclization
Wan, Changfeng,Gao, Linfeng,Wang, Qiang,Zhang, Jintang,Wang, Zhiyong
supporting information; experimental part, p. 3902 - 3905 (2010/11/04)
A practical and simple synthesis of 2,5-disubstituted oxazoles was developed via an iodine-catalyzed tandem oxidative cyclization. A wide range of common commercial aromatic aldehydes can be used as reaction substrates, which displayed excellent functional group compatibility in this reaction.
C-H bond activation: A versatile protocol for the direct arylation and alkenylation of oxazoles
Besselievre, Francois,Lebrequier, Sabrina,Mahuteau-Betzer, Florence,Piguel, Sandrine
experimental part, p. 3511 - 3518 (2010/02/28)
The versatile palladium, complex Pd(PPh3)4 catalyses both direct arylation and alkenylation of oxazoles efficiently. The method is regioselective and stereospecific with respect to bromoalkenes and tolerates a wide range of functional groups.
Stereoselective direct copper-catalyzed alkenylation of oxazoles with bromoalkenes
Besselievre, Francois,Piguel, Sandrine,Mahuteau-Betzer, Florence,Grierson, David S.
supporting information; experimental part, p. 4029 - 4032 (2009/06/18)
(Chemical Equation Presented) A copper-catalyzed direct alkenylation of oxazoles with bromoalkenes has been developed. The method is both regio- and stereoselective and tolerates a variety of functional groups. A wide range of 2-E-vinyl-substituted oxazoles were obtained in high yields including the highly fluorescent alkaloid annuloline.
