1410941-38-6Relevant academic research and scientific papers
Intramolecular Dehydrogenative Coupling Approach to 2-Oxindoles Using Fe(OAc)2/NaI/Na2S2O8
Zhao, Junyan,Song, Xun,Li, Dong,Zhao, Jinfeng,Qu, Jingping,Zhou, Yuhan
, p. 6392 - 6398 (2020/10/02)
Oxindole units are common structures that are featuring in natural products and drugs. A novel method for synthesizing 2-oxindoles from 1,3-dicarbonyl compounds based on ferrous salt and iodide catalyst was described. Using Fe(OAc)2/NaI/Na2S2O8, various 2-alkyl-3-phenylamino-3-oxopropanoates, bearing fluoro, chloro, bromo, alkyl, alkoxy, trifluoromethyl, cyano etc. on the benzene ring were converted smoothly into 2-oxindoles.
Electrochemical dehydrogenative cyclization of 1,3-dicarbonyl compounds
Wu, Zheng-Jian,Li, Shi-Rui,Long, Hao,Xu, Hai-Chao
, p. 4601 - 4604 (2018/05/14)
The intramolecular C(sp3)-H/C(sp2)-H cross-coupling of 1,3-dicarbonyl compounds has been achieved through Cp2Fe-catalyzed electrochemical oxidation. The key to the success of these dehydrogenative cyclization reactions is
Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C-H and sp3 C-H bonds
Kumar, Nivesh,Ghosh, Santanu,Bhunia, Subhajit,Bisai, Alakesh
supporting information, p. 1153 - 1169 (2016/07/06)
The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a 'transition-metal-free' intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon-carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for this reaction.
Palladium-catalyzed alcoholysis of 3-iodopropynamides: Selective synthesis of carbamoylacetates
Tang, Jian-Sheng,Guo, Can-Cheng
, p. 108 - 112 (2015/02/02)
A novel and selective method for the synthesis of carbamoylacetates via the alcoholysis of 3-iodopropynamides has been developed. 3-Iodopropynamides react with alcohols in the presence of palladium(II) acetate and DABCO to afford the corresponding carbamoylacetates in moderate to good yields.
DDQ-mediated direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious approach to the tetracyclic core of ergot alkaloids
Bhunia, Subhajit,Ghosh, Santanu,Dey, Dhananjay,Bisai, Alakesh
supporting information, p. 2426 - 2429 (2013/06/27)
An efficient route to 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position has been developed via a DDQ-mediated Intramolecular-Dehydrogenative-Coupling (IDC). The methodology involves a one-pot C-alkylation of β-N-arylamido esters (7) concomitant with dehydrogenative-coupling in the presence of stoichiometric amount of DDQ. A tentative mechanistic route has been proposed for the oxidative coupling. The methodology provides a two-step entry to the ergoline structure of ergot alkaloids.
Intramolecular dehydrogenative coupling of sp2 C-H and sp 3 C-H bonds: An expeditious route to 2-oxindoles
Ghosh, Santanu,De, Subhadip,Kakde, Badrinath N.,Bhunia, Subhajit,Adhikary, Amit,Bisai, Alakesh
supporting information, p. 5864 - 5867 (2013/02/22)
An intramolecular-dehydrogenative-coupling (IDC) using "transition- metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternary stereogenic center at the benzylic position. The methodology involves a one-pot C-alkylation of β-N-arylamido esters (3, 6) with alkyl halides using potassium tert-butoxide concomitant with a dehydrogenative coupling. A radical-mediated pathway has been tentatively proposed for the oxidative process.
