Highly Efficient Synthesis of Oxindole Derivatives Via Catalytic Intramolecular C-H Insertion Reactions of Diazoamides

2020 ◽  
Vol 840 ◽  
pp. 251-256 ◽  
Author(s):  
Phan Thi Thanh Nga ◽  
Masaya Tone ◽  
Hayato Inoue ◽  
Kazutaka Shibatomi ◽  
Seiji Iwasa

Oxindole derivatives were efficiently synthesized from diazoamides derived from aniline derivatives in the presence of a Ru(II)-Pheox catalyst. Ru(II)-Pheox was found to be one of the most efficient catalysts so far for the synthesis of oxindole derivatives from the diazoamides in high yields (up to 99%) with high regioselectivity. Furthermore, the reaction was rapid and no substituent effects on the aromatic ring.

2019 ◽  
Vol 17 (13) ◽  
pp. 3462-3470 ◽  
Author(s):  
Qiong Wu ◽  
Gui-Lin Li ◽  
Shuang Yang ◽  
Xiao-Qin Shi ◽  
Tian-Zi Huang ◽  
...  

An organocatalytic chemo- and regioselective C6-functionalization of 2,3-disubstituted indoles has been established via a reaction with ortho-hydroxybenzyl alcohols, which afforded biologically important diarylindol-6-ylmethanes in high yields.


2013 ◽  
Vol 37 (1) ◽  
pp. 19-21 ◽  
Author(s):  
Yimin Zhang ◽  
Iiu ◽  
Junmin Chen

A simple economical, and highly efficient catalytic system for the synthesis of diaryl sulfides by a copper-catalysed coupling of aryl halides and thioacetate in water has been developed. A variety of aryl halides reacted with thioacetate to give the desired products in high yields up to 95%. The present catalysis protocol tolerated a wide range of functional groups, including amino, fluoro, and carboxyl moieties.


2017 ◽  
Vol 41 (8) ◽  
pp. 448-451 ◽  
Author(s):  
Maryam Salari ◽  
Mohammad H. Mosslemin ◽  
Alireza Hassanabadi

A green and highly efficient synthesis of 12 novel trans-2-(4-chlorobenzoyl)-3-aryl-2,3-dihydronaphtho[2,3- b]furan-4,9-diones has been achieved via a three-component, one-pot condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with 2-hydroxy-1,4-naphthoquinone and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in water under reflux conditions. The advantages of this method are a short reaction time, high yields and the avoidance of any hazardous organic solvent. Therefore, this procedure can be classified as green chemistry.


2017 ◽  
Vol 53 (36) ◽  
pp. 5052-5055 ◽  
Author(s):  
Wenxuan Mao ◽  
Junji Zhang ◽  
Xin Li ◽  
Chen Li ◽  
He Tian

Regioisomerically pure multiaryl coronene bisimides (CBIs) are synthesized via a perylene tetraester precursor and IBr-mediated annelation with high yields.


SynOpen ◽  
2021 ◽  
Vol 05 (01) ◽  
pp. 91-99
Author(s):  
Raju Jannapu Reddy ◽  
Angothu Shankar ◽  
Md. Waheed

AbstractA highly efficient and eco-friendly method has been developed for the synthesis of allyl sulfones using Morita–Baylis–Hillman (MBH) adducts and thiosulfonates under mild conditions. The Cs2CO3-promoted radical sulfonylation provided a series of allyl sulfones in good to high yields with high stereoselectivities. A wide variety of MBH bromides/acetates as well as thiosulfonates were tolerated and reliable in scaled-up synthesis. A plausible mechanism is proposed to rationalize the radical sulfonylation.


2013 ◽  
Vol 9 ◽  
pp. 2129-2136 ◽  
Author(s):  
Akula Raghunadh ◽  
Satish S More ◽  
T Krishna Chaitanya ◽  
Yadla Sateesh Kumar ◽  
Suresh Babu Meruva ◽  
...  

A highly efficient synthesis of enantiomerically pure (S) and (R)-isomers of N-(2,3-dihydroxypropyl)arylamides has been developed with good overall yields in a two step process. The key step involves the ring opening of the chiral epoxide with a nitrogen heterocyclic carbene (NHC) and further rearrangement to chiral N-(2,3-dihydroxypropyl)arylamides in high yields and enantioselectivity. During the reaction, no erosion in chiral purity was observed.


2008 ◽  
Vol 86 (2) ◽  
pp. 124-128 ◽  
Author(s):  
J S Yadav ◽  
B.V. Subba Reddy ◽  
K Premalatha ◽  
K Shiva Shankar

2-Aryl-1-arylmethyl-1H-benzimidazoles are prepared in high yields under extremely mild conditions via the condensation of aryl-1,2-diamines with aromatic aldehydes using 10 mol% of bismuth triflate in water. The use of water and readily available bismuth triflate makes this process quite simple, more convenient, and environment-friendly.Key words: aryl-1,2-diamines, aromatic aldehydes, bismuth catalysis, benzimidazoles.


2014 ◽  
Vol 34 (1) ◽  
pp. 243-250
Author(s):  
Jianghong DING ◽  
Le XU ◽  
Hao XU ◽  
Haihong WU ◽  
Yueming LIU ◽  
...  

2013 ◽  
Vol 17 (3) ◽  
pp. 283-295 ◽  
Author(s):  
Jadwiga Soloducho ◽  
Joanna Cabaj ◽  
Kamila Olech ◽  
Przemyslaw Data ◽  
Mieczyslaw Lapkowski

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