58106-56-2Relevant academic research and scientific papers
Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes
Pitchumani, Venkatachalam,Breugst, Martin,Lupton, David W.
supporting information, p. 9413 - 9418 (2021/12/09)
β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.
3-Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of ortho-Functionalized Cinnamic Esters
Chaabouni, Slim,Simonet, Florent,Fran?ois, Alison,Abid, Souhir,Galaup, Chantal,Chassaing, Stefan
supporting information, p. 271 - 277 (2017/01/24)
A method for the trifluoromethylation of ortho-hydroxycinnamic esters was developed to achieve the regioselective synthesis of 3-trifluoromethylated coumarins. The reaction was performed by using the Togni reagent as the CF3source under mild conditions and showed good functional- group tolerance. The scope of this copper-mediated method was further expanded to the synthesis of 3-trifluoromethylated carbostyrils starting from ortho-aminocinnamic derivatives. Interestingly, a sequential one-pot synthesis of 3-trifluoromethylated coumarins starting from salicylaldehydes was further developed. The mechanism of this cascade reaction was explored, and a radical pathway was found to be consistent with the obtained results.
Synthesis of 2-Aryl-Substituted Indole-3-acetic Acid Derivatives via Intramolecular Imino-Stetter Reaction of Aldimines with Cyanide
Lee, Seong Jong,Seo, Hong-Ahn,Cheon, Cheol-Hong
supporting information, p. 1566 - 1570 (2016/10/13)
A general method to generate umpolung of aldimines with cyanide was developed via the addition of cyanide to aldimines followed by a proton transfer from the carbon atom to the nitrogen atom in the resulting cyanide adducts. This novel method was successf
Rhodium(III)-catalyzed in situ oxidizing directing group- assisted c-h bond activation and olefination: A route to 2-vinylanilines
Muralirajan, Krishnamoorthy,Haridharan, Radhakrishnan,Prakash, Sekar,Cheng, Chien-Hong
, p. 761 - 766 (2015/03/18)
A new and efficient method for the synthesis of 2-vinylanilines from the reaction of arylhydrazine hydrochlorides with alkenes and diethyl ketone via a rhodium-catalyzed C-H activation is described. The oxidant-free olefination reaction involves the in situ generation of an -N-N=CR1R2 moiety as the oxidizing directing group thus providing an easy access to 2-vinylanilines.
On water: Catalyst-free chemoselective synthesis of highly functionalized tetrahydroquinazolines from 2-aminophenylacrylate
Saunthwal, Rakesh K.,Patel, Monika,Tiwari, Rakesh K.,Parang, Keykavous,Verma, Akhilesh K.
supporting information, p. 1434 - 1441 (2015/03/18)
A green and catalyst-free atom-ecomonic straightforward tandem approach for the synthesis of highly functionalized tetrahydroquinazolines by the reaction of 2-aminophenylacrylates with isothiocyanates using water as an environmentally friendly solvent via amidation and concomitant chemoselective Michael-addition is described. This journal is
Cu(II)-catalyzed tandem synthesis of 2-imino[1,3]benzothiazines from 2-aminoaryl acrylates via thioamidation and concomitant chemoselective thia-Michael addition
Saunthwal, Rakesh K.,Patel, Monika,Kumar, Sushil,Verma, Akhilesh K.
supporting information, p. 677 - 681 (2015/01/30)
An efficient copper-catalyzed tandem approach for the synthesis of 2-imino[1,3]benzothiazines by the reaction of easily accessible 2-aminoaryl acrylates with isothiocyanates via in situ thioamidation and concomitant chemoselective intramolecular thia-Mich
A direct access to bioactive fused N-heterocyclic acetic acid derivatives
Adepu, Raju,Rajitha,Ahuja, Dipali,Sharma, Atul Kumar,Ramudu,Kapavarapu, Ravikumar,Parsa, Kishore V. L.,Pal, Manojit
supporting information, p. 2514 - 2518 (2014/04/17)
A Cu-catalyzed new sequence involving the Ullmann type intermolecular C-C followed by an intramolecular C-N coupling and then intramolecular aza-Michael type addition (and oxidation) in a single pot afforded various fused N-heterocyclic acetic acid derivatives as inhibitors of PDE4. This journal is the Partner Organisations 2014.
One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)
Lu, Xin-Mou,Li, Jian,Cai, Zhong-Jian,Wang, Rong,Wang, Shun-Yi,Ji, Shun-Jun
supporting information, p. 9471 - 9477 (2015/02/19)
An efficient and practical synthetic approach to access to 2H-pyrrolo[3,4-c]quinolin-4(5H)-one/2H-pyrrolo[3,4-c]quinoline derivatives by the reaction of 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC) via a one pot van Leusen rea
Organocatalytic enantioselective cascade aza-michael/michael addition for the synthesis of highly functionalized tetrahydroquinolines and tetrahydrochromanoquinolines
Yang, Wen,He, Hai-Xiao,Gao, Yu,Du, Da-Ming
supporting information, p. 3670 - 3678 (2014/01/06)
An efficient organocatalytic highly asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of tetrahydroquinolines and tetrahydrochromanoquinolines has been developed. This cascade reaction proceeds well at low catalyst loading with a broad substrate scope, furnishing the desired products in excellent yields with excellent diastereoselectivities and enantioselectivities (up to >99:1 dr, 99% ee) under mild conditions. Importantly, it is the first catalytic asymmetric method for tetrahydrochromanoquinolines. This protocol provides a straightforward entry to highly functionalized chiral tetrahydroquinoline and tetrahydrochromanoquinoline derivatives from simple starting materials. Copyright
An improved preparation of mesoporous silica-supported Pd as sustainable catalysts for phosphine-free Suzuki-Miyaura and Heck coupling reactions
Basu, Basudeb,Paul, Susmita
, p. 588 - 594 (2013/10/21)
An improved and eco-friendly procedure has been developed to generate mesoporous silica-supported palladium nanoparticles (SiO2@PdNP) that could be used as a sustainable heterogeneous Pd catalyst for phosphine-free Suzuki-Miyaura and Heck coupling reactions with excellent turnover number and turnover frequency. The presence of Pd on the silica surface was detected by X-ray diffraction and the structural morphology of SiO2@PdNP was obtained by transmission electron microscopy. The heterogeneous catalytic system is recyclable and leaching of the metal after the reaction is not apparently observed. Copyright
