The solvent-controlled chemoselective construction of C–S/S–S bonds via the Michael reaction/thiol coupling of quinoline-2-thiones

2019 ◽  
Vol 17 (9) ◽  
pp. 2379-2383 ◽  
Author(s):  
Xi Zhang ◽  
Tong-Lin Wang ◽  
Xiao-Jun Liu ◽  
Xi-Cun Wang ◽  
Zheng-Jun Quan

The solvent-controlled selective construction of C–S and S–S bonds containing a quinoline skeleton under mild conditions from quinoline-2-thiones has been reported.

1962 ◽  
Vol 40 (8) ◽  
pp. 1571-1575 ◽  
Author(s):  
R. L. Buchanan ◽  
F. H. Dean ◽  
F. L. M. Pattison

The synthesis of γ-fluoroglutamic acid, HOOCCHFCH2CH(NH2)COOH, was achieved by two independent methods, both of which involved the Michael reaction: (1) methyl α-fluoroacrylate and diethyl acetamidomalonate gave the transesterified intermediate, which on hydrolysis produced γ-fluoroglutamic acid (31% yield); (2) ethyl α-acetamidoacrylate and diethyl fluoromalonate reacted under mild conditions to give, after hydrolysis, the required amino acid in 56% overall yield. Of the two procedures, the second is preferable, since it is based on more readily available starting materials and gives a higher yield.


1996 ◽  
Vol 45 (1) ◽  
pp. 137-139
Author(s):  
I. E. Sokolov ◽  
A. S. Zanina ◽  
S. I. Shergina ◽  
M. S. Shvartsberg

2002 ◽  
Vol 79 (2) ◽  
pp. 264 ◽  
Author(s):  
Thomas Poon ◽  
Bradford P. Mundy ◽  
Thomas W. Shattuck

1968 ◽  
Vol 41 (10) ◽  
pp. 2519-2521 ◽  
Author(s):  
Kentaro Yoda ◽  
Takao Toda

2018 ◽  
Vol 74 (9) ◽  
pp. 1281-1284
Author(s):  
Thi Thanh Van Tran ◽  
Tuan Anh Le ◽  
Hong Hieu Truong ◽  
Thi Nhung Dao ◽  
Anatoly T. Soldatenkov ◽  
...  

The title compound, C30H34N2O9 (4), is a product of the Michael reaction of azacrown ether with dimethyl acetylenedicarboxylate modified by an addition of NH3 (aq.) at 298 K. The aza-14-crown-4-ether ring adopts a bowl conformation. The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 8.65 (5)°. The tetrahydropyridine ring has a boat conformation. The molecular conformation is supported by one N—H...O and two C—H...O intramolecular hydrogen bonds. Both heterocyclic and amino N atoms have essentially planar configurations (sums of the bond angles are 359.35 and 358.00°). Compound 4 crystallizes as a racemate consisting of enantiomeric pairs of the 1R,21S diastereomer. In the crystal, molecules of 4 are connected by N—H...O hydrogen bonds, forming chains along [100]. According to the PASS program (computer prediction of biological activities), compound 4 may exhibit antiallergic (72% probability) and antiasthmatic (67%) activity, as well as be a membrane permeability inhibitor (65%).


ChemInform ◽  
2010 ◽  
Vol 25 (26) ◽  
pp. no-no
Author(s):  
I. I. KANDROR ◽  
M. A. GALKINA ◽  
I. O. BRAGINA ◽  
B. D. LAVRUKHIN ◽  
YU. N. BELOKON' ◽  
...  

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