164290-83-9Relevant academic research and scientific papers
Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines
Neerathilingam, Nalladhambi,Bhargava Reddy, Mandapati,Anandhan, Ramasamy
supporting information, p. 15117 - 15127 (2021/10/25)
A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.
Nickel/Briphos-Catalyzed Direct Transamidation of Unactivated Secondary Amides Using Trimethylsilyl Chloride
Yu, Subeen,Shin, Taeil,Zhang, Maosheng,Xia, Yuanzhi,Kim, Hyunwoo,Lee, Sunwoo
supporting information, p. 7563 - 7566 (2019/01/03)
Direct transamidation of secondary amides was developed via nickel catalysis. In the presence of trimethylsilyl chloride and manganese, Ni(diglyme)Cl2 with a Briphos ligand efficiently promoted the transamidation of N-aryl benzamide derivatives with primary amines to afford the corresponding secondary amides in moderate to good yields. Primary amines bearing electron-donating groups gave higher yields of the transamidation products.
Design and development of benzoxazole derivatives with toll-like receptor 9 antagonism
Roy, Swarnali,Mukherjee, Ayan,Paul, Barnali,Rahaman, Oindrila,Roy, Shounak,Maithri, Gundaram,Ramya, Bandaru,Pal, Sourav,Ganguly, Dipyaman,Talukdar, Arindam
, p. 334 - 347 (2017/04/26)
Toll-like receptor 9 (TLR9) is a major therapeutic target for numerous inflammatory disorders. Development of small molecule inhibitors for TLR9 remains largely empirical due to lack of structural understanding of potential TLR9 antagonism by small molecules and due to the unusual topology of the ligand binding surface of the receptor. To develop a structural model for rational design of small molecule TLR9 antagonists, an enhanced homology model of human TLR9 (hTLR9) was constructed. Binding mode analysis of a series of molecules having characteristic molecular geometry, flexibility and basicity was conducted based on crystal structure of the inhibitory DNA (iDNA) bound to horse and bovine TLR9. Interaction with specific amino acid residues in four leucine rich repeat (LRR) regions of TLR9 was identified to be critical for antagonism by small molecules. The biological validation of TLR9 antagonism and its correlation with probe-receptor interactions led to a reliable model that could be used for development of novel small molecules with potent TLR9 antagonism (IC50 30–100?nM) with excellent selectivity against TLR7.
Exploiting the Reactivity of Isocyanide: Coupling Reaction between Isocyanide and Toluene Derivatives Using the Isocyano Group as an N1 Synthon
Liu, Zhiqiang,Zhang, Xinglu,Li, Jian,Li, Jianxiong,Li, Feng,Li, Chunju,Jia, Xueshun
, p. 4052 - 4055 (2016/08/30)
An unusual oxidative coupling reaction of isocyanide and toluene derivatives using tetrabutylammonium iodide (TBAI) as a catalyst is disclosed. The experimental results and mechanistic study show that the isocyano group acts formally as an N1 synthon during the transformation, thus expanding the reactivity profile of isocyanide.
Thermally induced cyclization of electron-rich N-arylthiobenzamides to benzothiazoles
Barrett, Oscene V.,Downer-Riley, Nadale K.,Jackson, Yvette A.
experimental part, p. 2579 - 2586 (2012/09/07)
Heating N-(2-methoxyphenyl)benzenecarbothioamides in refluxing nitrobenzene for 24 hours gives the corresponding benzothiazoles with intramolecular ipso substitution of the ortho-methoxy substituent. The thermal cyclization of various other N-arylthiobenzamides is also explored. Georg Thieme Verlag Stuttgart · New York.
Conversion of thiobenzamides to benzothiazoles via intramolecular cyclization of the aryl radical cation
Downer-Riley, Nadale K.,Jackson, Yvette A.
, p. 7741 - 7744 (2008/12/20)
A new and general method has been developed for the intramolecular cyclization of thiobenzamides to benzothiazoles via aryl radical cations as reactive intermediates. The method utilizes phenyliodine(III) bis(trifluoroacetate) (PIFA) in trifluoroethanol or cerium ammonium nitrate (CAN) in aqueous acetonitrile at room temperature to effect cyclization within 30 min in moderate yields.
