1006585-20-1Relevant articles and documents
The oxygen-mediated synthesis of 1,3-butadiynes in continuous flow: Using teflon AF-2400 to effect gas/liquid contact
Petersen, Trine P.,Polyzos, Anastasios,O'Brien, Matthew,Ulven, Trond,Baxendale, Ian R.,Ley, Steven V.
, p. 274 - 277 (2012)
The gas is always greener: A continuous flow Glaser-Hay coupling reaction system, mediated by molecular oxygen, is developed based on a tube-in-tube gas/liquid reactor/injector. The system uses a semi-permeable Teflon AF-2400 membrane to effect rapid gas/
Selective C-C coupling of terminal alkynes under an air atmosphere without base over Cu-NX-C catalysts
Xiao, Xinxin,Xu, Yin,Bhavanarushi, Sangepu,Liu, Bin,Lv, Xiaomeng
, p. 20993 - 20998 (2020)
The fabrication of a silk fibroin-drived porous, in situ nitrogenated carbon skeleton with highly dispersed Cu-NX-C active sites via a sol-gel and pyrolysis treatment was demonstrated. Cu-NX-C was used to catalyze the oxidative homo-coupling of terminal a
Synthesis of novel 8-(het)aryl-6H-pyrano[4′,3′:4,5]thieno[3,2-b]pyridines by 6-endo-dig cyclization of Sonogashira products and halolactonizations with Cu salts/NXS. Preliminary antitumor evaluation
Rodrigues, Juliana M.,Buisson, Pierre,Pereira, Joana M.,Pinheiro, Inês M.,Fernández-Marcelo, Tamara,Vasconcelos, M. Helena,Berteina-Raboin, Sabine,Queiroz, Maria-Jo?o R.P.
, p. 1387 - 1397 (2019)
Novel 8-(het)aryl-6H-pyrano[4′,3′:4,5]thieno[3,2-b]pyridines were prepared in good to high yields by a tandem one-pot procedure of Sonogashira coupling and 6-endo-dig lactonization from 3-bromothieno[3,2-b]pyridine-2-carboxylic acid and (het)arylalkynes. Sonogashira coupling products were also prepared from the corresponding methyl ester giving in the same reaction the corresponding 6-endo-dig compounds as minor products. The Sonogashira phenyl ester product gave cyclization with electrophiles only in low to moderate yields. Nevertheless, halolactonizations using Cu(I) or (II) salts/N-halosuccinimides (NXS) from either the phenyl ester or the carboxylic acid derivatives occurred in good to high yields. The growth inhibition potential of the compounds was evaluated using human tumor cell lines, HCT-15 (colorectal adenocarcinoma) and NCI-H460 (non-small cell lung cancer) and studies of apoptosis induction were performed for the three most promising compounds in HCT-15 cells. Two of them caused almost 40% of cell death by apoptosis when tested at their 1.5 × GI50 concentrations. The tricyclic lactone with a F atom in the meta position showed to be the most promising one.
Synergistic effect of bimetallic PdAu nanocrystals on oxidative alkyne homocoupling
Chen, Zheng,Shen, Rongan,Chen, Chen,Li, Jinpeng,Li, Yadong
, p. 13155 - 13158 (2018)
Bimetallic PdAu nanocrystals with different component ratios were obtained to investigate alkyne homocoupling. We found that the synergistic effect of Pd and Au plays an important role in the reaction. Alkynes with a variety of substituent groups could ef
Copper (II) catalyzed homocoupling and heterocoupling of terminal alkynes
Holganza, Maria Katrina,Trigoura, Leslie,Elfarra, Suzanne,Seo, Yoona,Oiler, Jeremy,Xing, Yalan
, p. 1179 - 1181 (2019)
Cu(OTf)2 catalyzed homo– and heterocoupling of aromatic and aliphatic terminal alkynes has been developed. Symmetric and unsymmetric 1,3-diynes have been synthesized in good yields under an aerobic condition in the presence of an organic base D
Cu-Catalyzed solvent-free, pot-economic synthesis of 1,3-dynes from 1,1-dibromoalkenes in the presence of DBU?H2O
Moodapelly, Shiva Krishna,Nanaji, Yerramsetti,Sharma, Gangavaram V.M.,Suneeel, Kanaparthy,Doddi, Venkata Ramana
, (2021/05/27)
An efficient synthesis of 1,3-diynes directly from 1,1-dibromoalkenes has been achieved by utilizing hydrated 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU.H2O) as a sole reagent and a catalyst CuI. In general, 1,3-diynes were synthesized from corresponding terminal alkynes, which in turn were obtained from 1,1-dibromoalkenes. The DBU.H2O allowed the synthesis of 1,3-diynes not only in a pot-efficient manner but also under solvent-free conditions at ambient temperature. A plausible mechanism is proposed via 1-bromoalkynes intermediate instead of terminal alkynes.
Synthesis of 8-carbo substituted 2-(trifluoromethyl)-4H-furo[2,3-h]chromen-4-ones and their thienoangelicin derivatives
Olomola, Temitope O.,Mphahlele, Malose J.
, (2019/12/03)
Tandem Sonogashira cross-coupling and heteroannulation of 7-hydroxy-8-iodo-2-(trifluoromethyl)chromen-4-one with terminal acetylenes afforded the 8-carbo–substituted 2-(trifluoromethyl)-4H-furo[2,3-h]chromen-4-ones 2a–i. The latter were reacted with methyl mercaptoacetate in the presence of triethylamine to afford the corresponding 7,8-dihydro-5H-furo[2,3-h]thieno[2,3-c]chromen-5-one derivatives 3a–i. The structures of the prepared compounds were characterized using a combination of NMR (1H-, 13C & 19F-), IR and mass spectroscopic techniques, and confirmed by single X-ray crystal structures of 8-(3-fluorophenyl)-2-(trifluoromethyl)-4H-furo[2,3-h]chromen-4-one (2b) and 2-phenyl-7-(trifluoromethyl)-7,8-dihydro-5H-furo[2,3-h]thieno[2,3-c]chromen-5-one (3a). The highlight of this investigation is the conversion of 2-(trifluoromethyl)–substituted 4H-furo[2,3-h]chromen-4-ones into trifluoromethyl–substituted thienoangelicin analogues.
