13131-02-7Relevant articles and documents
PhICl2/NH4SCN-Mediated Oxidative Regioselective Thiocyanation of Pyridin-2(1H)-ones
Tao, Shanqing,Xiao, Jiaxi,Li, Yadong,Sun, Fengxia,Du, Yunfei
, p. 2536 - 2546 (2021)
The reaction of pyridin-2(1H)-ones with PhICl2 and NH4SCN enables an efficient regioselective thiocyanation, leading to the synthesis of the biologically interesting C5 thiocyanated 2-pyridones in good to high yields. The mechanistic pathway of this metal-free approach is postulated to involve the formation of the reactive thiocyanogen chloride from the reaction of PhICl2 and NH4SCN followed with the regioselective electrophilic thiocyanation of the pyridin-2(1H)-one ring.
Structure Ligation Relationship of Amino Acids for the Amination Cross-Coupling Reactions
Vaidya, Gargi Nikhil,Khan, Arif,Verma, Hansa,Kumar, Sanjeev,Kumar, Dinesh
, p. 3004 - 3010 (2019)
The structure ligation relationship (SLR) of amino acids (AAs) for the cross-coupling aminations was examined. While AA ligated C-N cross-couplings under Pd and Ni catalysis were minor or ineffective, the AA ligated Cu-catalyzed C-N cross-couplings were promising particularly with the use of l-methionine. The roles of -NH2, -CO2H, and -S- of l-methionine were investigated and found critical for their ligation efficiency. The finding was compatible with aromatic as well as aliphatic amines including tautomerizable N-heteroarenes.
An unusual rearrangement involving 5-bromo-1-phenylpyridone during its methyl cross coupling with turbo-Grignard reagent, leading to a 5-bromopyridone-fused seven-membered carbocyclic ring
Falb, Eliezer,Ulanenko, Konstantin,Tor, Andrey,Afri, Michal,Gottlieb, Hugo,Hassner, Alfred
, p. 979 - 984 (2017)
[Figure not available: see fulltext.] The structure of a cyclohepta[c]pyridin-1-one, a product of an unusual transformation, isolated during a turbo-Grignard reagentpromoted methyl cross coupling to 5-bromo-1-phenyl-2-pyridone, was determined by 1H and 13C NMR, COSY and high-resolution MS, as well as computer modeling. Its formation suggests a remarkable nucleophilic attack at the α-position to the pyridone carbonyl group. A rational pathway is presented.
Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones
Chantarojsiri, Teera,Kittikool, Tanakorn,Phakdeeyothin, Kunita,Yotphan, Sirilata
supporting information, p. 3071 - 3078 (2021/07/22)
A highly efficient and regioselective manganese-induced radical oxidative direct C?P bond formation between 2-pyridones and secondary phosphine oxides was developed. The C3-selective phosphinoylation was conveniently achieved through a combination of substoichiometric manganese and persulfate oxidant under mild conditions. Various 3-phosphinoylated pyridone products can be obtained in moderate to high yields. Preliminary mechanistic studies suggest that the reaction is likely to involve a radical pathway induced by catalytically active Mn3+ species.
N - And O -arylation of pyridin-2-ones with diaryliodonium salts: Base-dependent orthogonal selectivity under metal-free conditions
Abe, Yusuke,Hanazawa, Natsumi,Katagiri, Kotone,Kuriyama, Masami,Ono, Shimpei,Onomura, Osamu,Yamamoto, Kosuke
, p. 8295 - 8300 (2020/09/09)
Metal-free N- and O-arylation reactions of pyridin-2-ones as ambident nucleophiles have been achieved with diaryliodonium salts on the basis of base-dependent chemoselectivity. In the presence of N,N-diethylaniline in fluorobenzene, pyridin-2-ones were very selectively converted to N-arylated products in high yields. On the other hand, the O-arylation reactions smoothly proceeded with the use of quinoline in chlorobenzene, leading to high yields and selectivities. In these methods, a variety of pyridin-2-ones in addition to pyridin-4-one and a set of diaryliodonium salts were accepted as suitable reaction partners.
