1141-45-3Relevant articles and documents
Cu(I)-Catalyzed Enantioselective Alkynylation of Thiochromones
Chang, Xiaoyong,Lin, Zhenyang,Meng, Ling,Ngai, Ka Yan,Wang, Jun
supporting information, p. 1155 - 1159 (2020/02/26)
A highly efficient asymmetric synthesis of chiral thiochromanones is developed via Cu(I)/phosphoramidite catalyzed asymmetric alkynylation of thiochromones under mild reaction conditions. The catalyst system is tolerant of various thiochromone precursors and terminal alkynes. The established asymmetric transformation provides different enatiomeric-enriched thiochromanones with more molecular complexity and enables access to chiral thioflavanones, a subgroup of flavonoid by further functionalization.
Development of conjugate addition of lithium dialkylcuprates to thiochromones: Synthesis of 2-alkylthiochroman-4-ones and additional synthetic applications
Bass, Shekinah A.,Parker, Dynasty M.,Bellinger, Tania J.,Eaton, Aireal S.,Dibble, Angelica S.,Koroma, Kaata L.,Sekyi, Sylvia A.,Pollard, David A.,Guo, Fenghai
supporting information, (2018/08/21)
Lithium dialkylcuprates undergo conjugate addition to thiochromones to afford 2-alkylthiochroman-4-ones in good yields. This approach provide an efficient and general synthetic approach to privileged sulfur-containing structural motifs and valuable precursors for many pharmaceuticals, starting from common substrates-thiochromones. Good yields of 2-alkyl-substituted thiochroman-4-ones are attained with lithium dialkylcuprates, lithium alkylcyanocuprates or substoichiometric amount of copper salts. The use of commercially available inexpensive alkyllithium reagents will expedite the synthesis of a large library of 2-alkyl substituted thiochroman-4-ones for additional synthetic applications.
Cu-Catalyzed Conjugate Addition of Grignard Reagents to Thiochromones: An Enantioselective Pathway for Accessing 2-Alkylthiochromanones
Luo, Shihui,Meng, Ling,Yang, Qingxiong,Wang, Jun
supporting information, p. 2071 - 2075 (2018/09/18)
The enantioselective incorporation of alkyl groups in thiochromones was realized for the first time by a Cu/(R, S)-PPF-P t Bu 2 -catalyzed conjugate addition of Grignard reagents to thiochromones. With this method, a series of 2-methylthiochromanones were obtained in good yields (up to 96% yield) with moderate-to-good ee values (up to 87% ee). The established method expedites the synthesis of a large library of chiral thiochromanones for further synthetic applications and biological studies.
Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones
Meng, Ling,Jin, Ming Yu,Wang, Jun
, p. 4986 - 4989 (2016/10/14)
A highly efficient asymmetric synthesis of chiral thioflavanones is developed via conjugate addition of arylzinc reagents to thiochromones using Rh(COD)Cl2/(R)-3,4,5-MeO-MeOBIPHEP catalyst. This method overcomes catalyst poisoning and substrate inertness and affords a series of chiral thioflavanones (2-arylthiochroman-4-ones) in good yields (up to 91% yield) with excellent ee values (up to 97% ee). The established asymmetric synthesis paves the way for further pharmaceutical studies.
Synthesis and biochemical evaluation of thiochromanone thiosemicarbazone analogues as inhibitors of cathepsin L
Song, Jiangli,Jones, Lindsay M.,Kumar, G. D. Kishore,Conner, Elizabeth S.,Bayeh, Liela,Chavarria, Gustavo E.,Charlton-Sevcik, Amanda K.,Chen, Shen-En,Chaplin, David J.,Trawick, Mary Lynn,Pinney, Kevin G.
experimental part, p. 450 - 453 (2012/09/25)
A series of 36 thiosemicarbazone analogues containing the thiochromanone molecular scaffold functionalized primarily at the C-6 position were prepared by chemical synthesis and evaluated as inhibitors of cathepsins L and B. The most promising inhibitors f
Fluoride ion-catalyzed conjugate addition for easy synthesis of 3-sulfanylpropionic acid from thiol and α,β-unsaturated carboxylic acid
Gao, Shijay,Tseng, Chi,Tsai, Cheng Hsuan,Yao, Ching-Fa
, p. 1955 - 1961 (2008/09/17)
3-Sulfanylpropionic acids are obtained in excellent yields by proceeding through a simple, mild, and efficient procedure utilizing tetrabutylammonium fluoride (TBAF) as catalyst.
Iodine catalyzed conjugate addition of mercaptans to α,β- unsaturated carboxylic acids under solvent-free condition
Gao, Shijay,Tzeng, Tingkai,Sastry,Chu, Cheng-Ming,Liu, Ju-Tsung,Lin, Chunchi,Yao, Ching-Fa
, p. 1889 - 1893 (2007/10/03)
We have described herein molecular iodine catalyzed Michael addition of thiol to α,β-unsaturated carboxylic acids. This environmentally benign catalytic system (iodine) used under mild and solvent-free conditions to achieve the corresponding adducts in excellent yield.
CONFORMATIONAL ANALYSIS AND PHOTOCHeMICAL BEHAVIOUR OF SULFOXIDES IN THE NAPHTHOTHIOPYRAN AND NAPHTHOTHIOPYRAN SERIES
Still, Ian W. J.,Arora, Parkash C.,Hasan, S. Khaquan,Kutney, Gerald W.,Lo, LAwrence Y. T.,Turnbull, Kenneth
, p. 199 - 209 (2007/10/02)
The sulfoxides derived from 2,3-dihydro-4H-naphthothiopyran and its 4-phenyl and 4-oxo derivatives, as well as the analogous sulfoxides in the 2,3-dihydro-1H-naphthothiopyran series, have been synthesized and their structures established by spectroscopic methods, especially 1H and 13C nmr.On the photolysis these sulfoxides have been found to react by a rather inefficient photochemical deoxygenation pathway.
