85903-33-9Relevant academic research and scientific papers
Substrate-Controlled Divergent Synthesis of Enaminones and Pyrroles from Indolizines and Nitroso Compounds
González-Soria, María José,Alonso, Francisco
, p. 5005 - 5017 (2019/11/03)
It is imperative to learn new synthetic transformations to succeed in drug discovery and development. We report the substrate-driven synthesis of β-enaminones and N-aryl pyrroles from indolizines and nitrosoarenes; aryl-substituted indolizines lead to β-enaminones in a regio- and diastereoselective manner, whereas alkyl-substituted indolizines produce tetrasubstituted pyrroles. All products contain a pyridine unit, the second most abundant ring (after phenyl) in the FDA Orange Book. In both cases, the reactions proceed at room temperature without any catalyst. Moreover, both types of products can be obtained in one pot from commercial materials as well as at a gram scale. It is worthy of note that the regioselectivity of the β-enaminones is inaccessible by the standard literature methods and their utility has been exemplified in the synthesis of diverse heterocycles. We have made every endeavor to put forward the corresponding reaction mechanisms based on thorough experimental work. (Figure presented.).
Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes
Jawalekar, Anup M.,Reubsaet, Erik,Rutjes, Floris P. J. T.,Van Delft, Floris L.
, p. 3198 - 3200 (2011/05/05)
Treatment of oximes with hypervalent iodine leads to substituted isoxazoles via rapid formation of nitrile oxides. Reaction with terminal alkynes led to a series of 3,5-disubstituted isoxazoles with complete regioselectivity and high yield, in a procedure
Photoinduced ring transformation of pyrido-[1,2-b]pyridazinium-4-olate
Batori, Sandor,Doepp, Dietrich,Messmer, Andras
, p. 4699 - 4708 (2007/10/02)
The photolytic behavior of the zwitterionic pyrido[1,2-b]pyridazinium-4- olate (1) was studied. A marked difference was observed depending on the wavelength used: irradiation with a light of λ>280 nm resulted in 3-phenyl- 5-(2-pyridyl)isoxazole (2) and 2-phenyl-3-(2-pyridylcarbonyl)azirine (3) as main products, while the use of light of λ280 afforded 2-phenyl-5-(2- pyridyl)-oxazole (5) and 1-amino-1-phenyl-3-(2-pyridyl)prop-1-en-3-one (6) as main products. A mechanistic suggestion is provided.
STUDIES ON ISOMERIC PYRIDYLISOXAZOLES
Belgodere, Elena,Bossio, Ricardo,Sio, Francesco De,Marcaccini, Stefano,Pepino, Roberto
, p. 501 - 504 (2007/10/02)
Data concerning the reaction between hydroxylamine hydrochloride and 1-(2-pyridyl)-3-phenyl- (I a) and 1-(2-thienyl)-3-phenyl-1,3-propanedione (I l) disagree with those previously reported in literature.The same reaction was also studied employing a series of 1,3-diketones-1-(pyridyl)-substituted I b-i.The direction of enolization of 1,3-diketones accounted for the isomeric isoxazoles formation.
