54758-71-3

Upstream product

• 611-20-1 salicylonitrile 
• 117-99-7 2-Hydroxybenzophenone 

Downstream Products

• 16560-26-2 2-oxo-4-phenyl-2H-chromene-3-carbonitrile 
• 15185-05-4 4-phenylcoumarin 
• 1025506-23-3 (S)-2-(amino(phenyl)methyl)phenol 
• 780038-05-3 rac-2-[amino(phenyl)methyl]phenol 
• 833-50-1 2-phenylbenzo[d]oxazole 
• 7007-67-2 3-phenyl-1,2-benzisoxazole 

Relevant academic research and scientific papers

2-Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis

An organocatalytic system is presented for the Michael addition of monoactivated glycine ketimine ylides with a bifunctional catalyst. The ketimine bears an ortho hydroxy group, which increases the acidity of the methylene hydrogen atoms and enhances the reactivity, thus allowing the synthesis of a large variety of α,γ-diamino acid derivatives with excellent stereoselectivity.

Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines

N-Unprotected ketimines are useful substrates and intermediates for synthesizing valuable nitrogen-containing compounds, but their potential applicability is limited by the available synthetic methods. To address this issue, we report a scandium(III) triflate catalyzed direct synthesis of N-unprotected ketimines. Using commercially available reagents and Lewis acid catalysts, ketones were directly transformed into the corresponding N-unprotected ketimines in high yields with broad functional group tolerance, even in multigram scales. The reactions were readily applicable for one-pot synthesis of important compounds such as a glycine Schiff base without isolation of N-unprotected ketimine intermediates. Preliminary mechanistic studies to clarify the reaction mechanism are also described.

Asymmetric Transfer Hydrogenation of o-Hydroxyphenyl Ketones: Utilizing Directing Effects That Optimize the Asymmetric Synthesis of Challenging Alcohols

A systematic range of o-hydroxyphenyl ketones were reduced under asymmetric transfer hydrogenation conditions using the C3-tethered catalyst 2. Two directing effects, i.e., an o-hydroxyphenyl coupled to a bulky aromatic on the opposite side of the ketone substrate, combine in a matched manner to deliver reduction products with very high enantiomeric excess.

Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2

A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.

Intramolecular hydrogen-bond activation for the addition of nucleophilic imines: 2-hydroxybenzophenone as a chemical auxiliary

The addition of nucleophilic imines, using 2-hydroxybenzophenone as a chemical auxiliary, is presented. An intramolecular six-membered ring via hydrogen bonding that enhances the reactivity and selectivity is the key of this strategy, which is supported b

Chiral phosphoric acid catalyzed enantioselective transfer hydrogenation of ortho-hydroxybenzophenone N-H ketimines and applications

Unprotected synthesis: The first enantioselective chiral phosphoric acid catalyzed transfer hydrogenation of unprotected ortho-hydroxybenzophenone N-H imines by using a Hantzsch ester as the hydrogen source afforded the corresponding chiral N,O-unprotected ortho-hydroxydiarylmethylamines in high yields with excellent enantioselectivities (see scheme).

A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine

A divergent and regioselective synthesis of either 3-substituted benzisoxazoles or 2-substituted benzoxazoles from readily accessible ortho-hydroxyaryl N-H ketimines is described. The reaction proceeds in two distinct pathways through a common N-Cl imine intermediate: (a) N-O bond formation to form benzisoxazole under anhydrous conditions and (b) NaOCl mediated Beckmann-type rearrangement to form benzoxazole, respectively. The reaction path also depends on the electronic nature of the aromatic ring, with the electron-rich aromatic rings favoring the rearrangement and the electron-deficient rings favoring the N-O bond formation. A Beckmann-type rearrangement mechanism via net [1,2]-aryl migration for the formation of 2-substituted benzoxazole is proposed.

Microwave-promoted, one-pot, solvent-free synthesis of 4-arylcoumarins from 2-hydroxybenzophenones

4-Arylcoumarins are synthesized in very good yields through solvent-free microwave irradiation of 2-hydroxybenzophenones and alkyl malonate in the presence of DBU. The onepot synthesis is carried out with Knoevenagel condensation, intramolecular lactonization, and decarboxylation reactions. The method can be applied to a broad scope of neoflavonoids.

Process development of potassium channel opener, TCV-295, based on convenient ring formation of 2H-1,3-benzoxazine and selective N-oxidation of the pyridyl moiety

An efficient process for potassium channel opener, TCV-295, based on a novel and convenient 4-(2-pyridyl)-2H-1,3-benzoxazine ring formation from o-hydroxybenzoylpyridine by the NH4I/piperidine/2,2-dimethoxypropane system and the following selective pyridine-N-oxidation using dimethyldioxirane, has been developed. Additionally, the combination reagent of ammonium halide and sec- or tert- amine conveniently converted o-hydroxyphenyl arylketones with several ketones (or benzaldehyde) to various novel 4-aryl-2H-1,3-benzoxazines.