109520-25-4Relevant academic research and scientific papers
The cooperative effect of Lewis pairs in the Friedel-Crafts hydroxyalkylation reaction: A simple and effective route for the synthesis of (±)-carbinoxamine
Harikrishnan, Adhikesavan,Sanjeevi, Jayakumar,Ramanathan, Chinnasamy Ramaraj
, p. 3633 - 3647 (2015/03/30)
An efficient C-C bond formation strategy between aromatic/heteroaromatic π-nucleophiles and Lewis acid activated aldehydes is described. This aromatic electrophilic substitution reaction of arenes or heteroarenes is facilitated by Lewis acid AlBr3. Aromatic rings with electron donating substituents are excellent nucleophilic counterparts in this reaction, generating carbinols in excellent yields (61-94%). The formation of triarylmethanes is also witnessed in the case of certain reactive aldehydes and aromatic π-nucleophiles through reactive carbocation formation. The formation of triarylmethane is reduced to a greater extent via retardation of the second π-nucleophile addition through a Lewis base, for example, pyridine, coordination with an aluminium alkoxide intermediate. Various aliphatic aldehydes also underwent Friedel-Crafts type hydroxyalkylation and generated the expected carbinols in moderate yields (41-53%) in the presence of AlBr3. This protocol has been successfully applied to the synthesize of the (±)-carbinoxamine, a therapeutically important histamine H1 antagonist, in a one-pot manner.
Effective dehydrogenation of 2-pyridylmethanol derivatives catalyzed by an iron complex
Kamitani, Masahiro,Ito, Masaki,Itazaki, Masumi,Nakazawa, Hiroshi
supporting information, p. 7941 - 7944 (2014/07/08)
An unprecedented iron complex-catalyzed dehydrogenation of alcohols was achieved using CpFe(CO)2Cl with a base or CpFe(CO)(Py)(Ph) as a catalyst without sacrificing the hydrogen acceptors. This reaction effectively (up to TON 67000) converted 2-pyridylmethanol derivatives to the corresponding ketones or aldehydes. The mechanistic study is also discussed. the Partner Organisations 2014.
Pyridylmagnesiates: Generation by bromine-metal exchange and enantioselective addition to aldehydes
Catel, Delphine,Payen, Olivier,Chevallier, Floris,Mongin, Florence,Gros, Philippe C.
experimental part, p. 4018 - 4028 (2012/07/28)
Butyl and dibutylmagnesiates incorporating chiral ligands have been prepared and their reactivity studied. The reagents were efficient to promote the clean bromine-magnesium exchange of azinyl bromides at room temperature and subsequent reaction with aldehydes affording pyridylcarbinols. (R,R)-TADDOL-based dibutylmagnesiate was the best reagent leading to acceptable to good enantioselectivities, depending on the substrate and on the aldehyde substitution. This is the first example of enantioselective addition of in situ generated pyridylmagnesiate to carbonyl electrophiles.
Synthesis of fluorescent 1,3-diarylated imidazo[1,5-α]pyridines: Oxidative condensation-cyclization of aryl-2-pyridylmethylamines and aldehydes with elemental sulfur as an oxidant
Shibahara, Fumitoshi,Sugiura, Rie,Yamaguchi, Eiji,Kitagawa, Asumi,Murai, Toshiaki
supporting information; experimental part, p. 3566 - 3568 (2009/09/05)
Oxidative condensation - cyclization of aldehydes and aryl-2- pyridylmethylamines proceeded in the presence of a stoichiometric amount of elemental sulfur as an oxidant in the absence of catalyst. The reaction gave a variety of 1,3-diarylated imidazo[l,5-a]pyridines in good to high yields. The products showed fluorescence emission in a wavelength range of 454-524 nm. The quantum yields of 1,3-diarylated imidazopyridines were greatly improved compared to those of the parent 3-monosubstituted compounds.
