Iodine-mediated aryl transfer reaction from arylhydrazine hydrochlorides to nitriles
An iodine-promoted, metal-, base-, and solvent-free cross-coupling reaction was developed for the synthesis of various useful secondary amides via an aryl N-addition reaction of aryl groups to cyano groups. This aryl transfer reaction proceeds with arylhydrazine hydrochlorides serving as the aryl donors. A labelling experiment shows that the N atom in the product comes from the cyano group of the nitriles, which are low in cost. A plausible radical-driven mechanism is also proposed.
Practical preparation of challenging amides from non-nucleophilic amines and esters under flow conditions
A fast and efficient protocol for the formation of amides from low nucleophilic amines and esters in flow is described. Products were obtained in good to excellent yields and with the advantage of simultaneous mixing of all reagents at once, avoiding steps for intermediate formation. The protocol is also suitable to be combined with ester synthesis, resulting in the preparation of amides in-line from haloarenes. This journal is
Vrijdag, Johannes L.,Delgado, Francisca,Alonso, Nerea,De Borggraeve, Wim M.,Prez-Macias, Natalia,Alczar, Jesus
supporting information
p. 15094 - 15097
(2014/12/11)
Imidazopyridazines and an Imidazopyrazine from Pyridazin- and Pyrazin-amines
The ambiguous condensations of phenylglyoxal with pyridazin-3-amines and pyrazin-2-amine are shown to yield 2-phenylimidazopyridazin-3(5H)-ones and imidazopyrazin-3(7H)-one, respectively.The former products exist as such, at least in the solid state, whereas the latter product exists to a large extent as the corresponding dipolar molecule.The reactions, degradations and n.m.r. spectra of the products are discussed.
Barlin, Gordon B.,Brown, Desmond J.,Kadunc, Zdenka,Petric, Andrej,Stanovnik, Branko,Tisler, Miha
p. 1215 - 1220
(2007/10/02)
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