149268-07-5Relevant articles and documents
Solvent-free synthesis of hydrazones and their subsequent N-alkylation in a Ball-mill
Nun, Pierrick,Martin, Charlotte,Martinez, Jean,Lamaty, Frédéric
supporting information; experimental part, p. 8187 - 8194 (2011/10/31)
A large variety of Boc-, Bz-, Ts-, and Fmoc- protected hydrazones were prepared via condensation of an equimolar amount of carbonyl-compound and the corresponding hydrazine using a ball-mill. Hydrazones were always obtained in a quantitative yield and no solvents were used at any step. In a second step, we realized the first solvent-free N-allylation and N-benzylation of these hydrazones.
Stereoselective synthesis of cis- or trans-3,5-disubstituted pyrazolidines via pd-catalyzed carboamination reactions: Use of allylic strain to control product stereochemistry through N-substituent manipulation
Giampietro, Natalie C.,Wolfe, John P.
supporting information; experimental part, p. 12907 - 12911 (2009/03/12)
The stereoselective synthesis of either trans- or cis-3,5-disubstituted pyrazolidines is accomplished via Pd-catalyzed carboamination reactions of unsaturated hydrazine derivatives. The products are obtained in good yield with up to >20:1 diastereoselectivity. Stereocontrol is achieved by modulating the degree of allylic strain in the transition state for syn-aminopalladation through a simple modification of the substrate N2-substituent. The pyrazolidine products can be further transformed to 3,5-disubstituted pyrazolines via deprotection/oxidation, or to substituted 1,3-diamines via N-N bond cleavage.
Palladium-catalyzed synthesis of aryl ketones by coupling of aryl bromides with an acyl anion equivalent
Takemiya, Akihiro,Hartwig, John F.
, p. 14800 - 14801 (2008/02/05)
Palladium-catalyzed couplings of aryl bromides with N-tert-butylhydrazones as acyl anion equivalents to form aryl ketones are reported. The coupling process occurs at the C-position of hydrazones to form N-tert-butyl azo compounds. Isomerization of these azo compounds to the corresponding hydrazones, followed by hydrolysis, gave the desired mixed alkyl aryl ketones. The selectivity of C- versus N-arylation was strongly influenced by the substituent on nitrogen. Arylation at carbon occurred with N-tert-butylhydrazones, whereas N-arylation occurred with N-arylhydrazones. The arylation of hydrazones containing primary and secondary alkyl groups, as well as aryl groups, gave the desired ketones in good yields after hydrolysis. Functional groups on the aromatic ring, such as alkoxy, cyano, trifluoromethyl, carboalkoxy, carbamoyl, and keto groups, were tolerated. This reaction likely occurs by C-C bond-forming reductive elimination from an intermediate containing an η1-diazaallyl ligand. Copyright
Novel azapeptide inhibitors of hepatitis C virus serine protease
Bailey, Murray D.,Halmos, Ted,Goudreau, Nathalie,Lescop, Ewen,Llinàs-Brunet, Montse
, p. 3788 - 3799 (2007/10/03)
Azapeptides are known inhibitors of several serine and cysteine proteases. In seeking different classes of inhibitors for the HCV serine protease, a series of novel azapeptide-based inhibitors were investigated which incorporated noncleavable P1/P1′ aza-a
