200930-72-9Relevant academic research and scientific papers
Synthesis of Pyridylsulfonium Salts and Their Application in the Formation of Functionalized Bipyridines
Duong, Vincent K.,Horan, Alexandra M.,McGarrigle, Eoghan M.
supporting information, p. 8451 - 8457 (2020/11/12)
An S-selective arylation of pyridylsulfides with good functional group tolerance was developed. To demonstrate synthetic utility, the resulting pyridylsulfonium salts were used in a scalable transition-metal-free coupling protocol, yielding functionalized bipyridines with extensive functional group tolerance. This modular methodology permits selective introduction of functional groups from commercially available pyridyl halides, furnishing symmetrical and unsymmetrical 2,2′- A nd 2,3′-bipyridines. Iterative application of the methodology enabled the synthesis of a functionalized terpyridine with three different pyridine components.
Selective Functionalization of Aminoheterocycles by a Pyrylium Salt
Moser, Daniel,Duan, Yaya,Wang, Feng,Ma, Yuanhong,O'Neill, Matthew J.,Cornella, Josep
supporting information, p. 11035 - 11039 (2018/07/31)
The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry-BF4) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C?N bond for nucleophilic aromatic substitution. More than 60 examples for the formation of C?O, C?N, C?S, or C?SO2R bonds are disclosed herein. In contrast to C?N activation through diazotization and polyalkylation, this method is characterized by its mild conditions and impressive functional-group tolerance. In addition to small-molecule derivatization, Pyry-BF4 allows the introduction of functional groups in a late-stage fashion to furnish highly functionalized structures.
Nucleophilic substitutions at the pyridine ring. Conformational preference of the products and kinetics of the reactions of 2-chloro-3-nitro- and 2-chloro-5-nitro-pyridines with arenethiolates
Hamed, Ezzat A.,El-Bardan, Ali A.,Saad, Esmat F.,Gohar, Gamal A.,Hassan, Ghada M.
, p. 2415 - 2421 (2007/10/03)
The reactions of 2-chloro-3-nitropyridine 1 and 2-chloro-5-nitropyridine 2 with arenethiolates 3a-i result in arylthio-dechlorination to give 2-arylthio-3-nitropyridines 4a-i and 2-arylthio-5-nitropyridines 5a-i. A 1H NMR study and AM1 calculat
