300401-95-0Relevant academic research and scientific papers
Singlet oxygen mediated dual C-C and C-N bond cleavage in visible light
Jain, Nidhi,Kumar, Sharvan,Ritu,Sharma, Charu
, p. 2921 - 2928 (2020/04/28)
A tandem cleavage of carbon-carbon and carbon-nitrogen bonds in imidazo[1,2-a]pyridines and imidazo[1,2-a]quinolines is reported in the presence of eosin Y and visible light. The ring opening occurs under ambient conditions through singlet oxygen insertio
N-Heterocyclic Carbene-Catalyzed Mannich Reaction for the Synthesis of β-Amino Ketones: N,N-Dimethylformamide as Carbon Source
Alanthadka, Anitha,Devi, E. Sankari,Selvi, A. Tamil,Nagarajan, Subbiah,Sridharan, Vellaisamy,Maheswari, C. Uma
supporting information, p. 2369 - 2374 (2017/07/22)
The efficiency of N,N-dimethylformamide (DMF) in the N-heterocyclic carbene-catalyzed Mannich reaction for the synthesis of β-amino ketones has been demonstrated. This strategy involves oxidative coupling of aryl methyl ketones and 2-aminopyridines in the presence of DMF. The reaction does not require pre-functionalization of the substrates, thus making it a practically applicable approach for the generation of β-amino ketones. The reaction requires the use of tin(II) chloride dihydrate (SnCl2?2 H2O) as Lewis acid in the presence of tert-butyl hydroperoxide (TBHP) as the oxidant. The reaction was tolerant to several aryl methyl ketones, including 2-acetylnaphthalene and acetylthiophene. Various substituted 2-aminopyridines react with acetophenone to give the desired β-amino ketones in good yields. (Figure presented.).
Metal-free TBHP-mediated oxidative ring openings of 2-arylimidazopyridines via regioselective cleavage of C-C and C-N bonds
Yan, Kelu,Yang, Daoshan,Wei, Wei,Li, Guoqing,Sun, Mingyang,Zhang, Qingyun,Tian, Laijin,Wang, Hua
, p. 100102 - 100105 (2015/12/05)
A highly regioselective TBHP-mediated ring opening of imidazopyridines via cleavage of C-C and C-N bonds has been achieved for the first time to afford N-(pyridin-2-yl)benzamides. Preliminary mechanistic investigations revealed that the present metal-free
A one-pot copper catalyzed biomimetic route to n -heterocyclic amides from methyl ketones via oxidative c-c bond cleavage
Subramanian, Parthasarathi,Indu, Satrajit,Kaliappan, Krishna P.
supporting information, p. 6212 - 6215 (2015/01/09)
A direct one-pot Cu-catalyzed biomimetic oxidation of methyl ketones to pharmaceutically important N-heterocyclic amides is reported. The scope of the method is broad, scalable, and mild, and the reaction is tolerant with various acid, base sensitive functionalities with multiple heteroatoms and aryl halides. The extensive mechanistic studies suggest that this reaction follows the Luciferin-Luciferase-like pathway.
Synthesis of cytimidine through a one-pot copper-mediated amidation cascade
Serrano, Catherine M.,Looper, Ryan E.
supporting information; experimental part, p. 5000 - 5003 (2011/11/13)
A concise synthesis of cytimidine was developed utilizing tandem Cu-mediated N-aryl amidations followed by global deprotection. This sequence exploits a regioselective coupling of an iodobenzamide with a halopyrimidine that allows the union of three fragments in a single synthetic manipulation and will permit the efficient and rapid diversification of the cytimidine core.
