4439-11-6Relevant academic research and scientific papers
Aminofluorene-Mediated Biomimetic Domino Amination-Oxygenation of Aldehydes to Amides
Ghosh, Santanu,Jana, Chandan K.
supporting information, p. 5788 - 5791 (2016/11/29)
A conceptually novel biomimetic strategy based on a domino amination-oxygenation reaction was developed for direct amidation of aldehydes under metal-free conditions employing molecular oxygen as the oxidant. 9-Aminofluorene derivatives acted as pyridoxamine-5′-phosphate equivalents for efficient, chemoselective, and operationally simple amine-transfer oxygenation reaction. Unprecedented RNH transfer involving secondary amine to produce secondary amides was achieved. In the presence of 18O2, 18O-amide was formed with excellent (95%) isotopic purity.
Cascade reaction of propargylic alcohols with hydroxylamine hydrochloride: facile synthesis of α,β-unsaturated oximes and nitriles
Zhang, Qi,Zhang, Linjing,Tang, Chaojun,Luo, Huan,Cai, Xuediao,Chai, Yonghai
, p. 6935 - 6942 (2016/10/14)
We have developed an easy and practical method for the synthesis of α,β-unsaturated oximes and nitriles from readily available propargylic alcohols with hydroxylamine hydrochloride (NH2OH·HCl) under metal-free conditions. By using or not using p-toluenesulfonyl chloride (p-TsCl) as the dehydrating promoter, the desired nitriles or oximes could be obtained, respectively via a three-step one-pot or two-step one-pot process in moderate to excellent yields with good functional group compatibility.
Tandem-type Pd(ii)-catalyzed oxidative Heck reaction/intramolecular C-H amidation sequence: A novel route to 4-aryl-2-quinolinones
Inamoto, Kiyofumi,Kawasaki, Junpei,Hiroya, Kou,Kondo, Yoshinori,Doi, Takayuki
, p. 4332 - 4334 (2012/05/20)
A novel catalytic method for synthesizing 4-aryl-2-quinolinones is reported. The process involves two mechanistically independent, sequential Pd(ii)-catalyzed reactions - the oxidative Heck reaction and the intramolecular C-H amidation - both of which smoothly proceed in the presence of a single catalytic system in a one-pot manner. The Royal Society of Chemistry 2012.
4-Aryl-2-quinolones from 3,3-diarylacrylamides through intramolecular copper-catalyzed C-H functionalization/C-N bond formation
Berrino, Roberta,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella
experimental part, p. 2537 - 2542 (2012/05/05)
Free NH 3,3-diarylacrylamides are cyclized to substituted 2-quinolones in the presence of CuI, PPh3, and KO-t-Bu in o-xylene at 100 °C. The reaction proceeds through a C-H functionalization/C-N bond formation process. With unsymmetrical 3,3-diarylacrylamides, high selectivity is observed using substrates where the aromatic ring trans to the amide group bears o-methyl, -chloro, or -bromo substituents.
Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles mediated by manganese(III) acetate
Yilmaz, E. Vildan Burgaz,Yilmaz, Mehmet,Oektemer, Atilla
, p. 363 - 376 (2011/09/20)
Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles in presence of manganese(III) acetate produced ethyl 4-cyano-2,3-dihydrofuran-3-carboxylates and 4-cyano-2,3-dihydrofuran-3- carboxamides in good yields. The radical cyclizations of conjugated amides gave 2,3-dihydrofurans in better yields than that of conjugated esters. Moreover, the reactions of thienyl substituted amides and esters with 3-oxopropanenitriles afforded 2,3-dihydrofurans more efficiently than phenyl substituted ones. ARKAT-USA, Inc.
Palladium-catalyzed intramolecular amidation of C(sp2)-H bonds: Synthesis of 4-aryl-2-quinolinones
Inamoto, Kiyofumi,Saito, Tadataka,Hiroya, Kou,Doi, Takayuki
supporting information; experimental part, p. 3900 - 3903 (2010/07/05)
Figure presented A catalytic synthetic approach for the synthesis of 2-quinolinone compounds through a Pd-catalyzed C(sp2)-H functionalization/intramolecular amidation sequence is described. The cyclization process efficiently proceeds in the p
Palladium-Catalyzed Conjugate Addition Type Reaction of Aryl Iodides with α,β-Unsaturated Ketones
Cacchi, S.,Arcadi, A.
, p. 4236 - 4240 (2007/10/02)
Aryl iodides have been found to react with α,β-unsaturated ketones in the presence of catalytic amounts of palladium, an excess of formic acid, and triethylamine, giving rise to conjugate addition type products.The electron-withdrawing power of the group attached to the olefinic double bond, the substituent β to the carbonyl group, and the basic reaction medium appear to effect greatly the conjugate addition/vinylic substitution ratio.
