Synthesis and characterization of 2-(anthracene-9-yl)-4,5-diphenyl-1-imidazole derivatives as environmentally sensitive fluorophores.

2-(Anthracene-9-yl)-4,5-diphenyl-1-imidazole (ADPI) provides an intriguing molecular platform for developing organic fluorophores with diverse properties and fluorescence performances. However, derivatives of ADPI have not yet been well explored and extensive studies are warranted. To shed more light on this, we have synthesized a series of π-extended ADPIs through a concise synthetic route involving an efficient cross-condensation reaction followed by Pd-catalyzed Suzuki cross-coupling.

Direct Formation of 2-Substituted 2-Indazoles by a Pd-Catalyzed Reaction between 2-Halobenzyl Halides and Arylhydrazines.

A direct and operationally simple method for the regioselective synthesis of 2-aryl-substituted 2-indazoles is reported. The Pd-catalyzed reaction between easily available 2-bromobenzyl bromides and arylhydrazines employing CsCO as the base and -BuPHBF as the ligand in DMSO at 120 °C in a sealed tube delivers the 2-substituted-2-indazoles in a single synthetic step with yields up to 79%. The new method is based on a regioselective intermolecular -benzylation followed by intramolecular -arylation and oxidation.

Base-Promoted Domino Reaction of 5-Substituted 2-Nitrosophenols with Bromomethyl Aryl Ketones: A Transition-Metal-Free Approach to 2-Aroylbenzoxazoles.

The reaction of 5-substituted 2-nitrosophenols with bromomethyl aryl ketones and related compounds employing K2CO3 as a base in refluxing THF and DMF at 80 °C, respectively, delivers 2-aroylbenzoxazoles in a single step with yields up to 85%. The new method involves an intermolecular nucleophilic substitution followed by intramolecular 1,2-addition and elimination. It allows an efficient and practical access to 2-aroylbenzoxazoles under transition-metal-free conditions.

Synthesis of 2-aryl-1,2-dihydrophthalazines via reaction of 2-(bromomethyl)benzaldehydes with arylhydrazines.

The reaction of 2-(bromomethyl)benzaldehydes with arylhydrazines employing K(2)CO(3) as a base and FeCl(3) as a catalyst in CH(3)CN at 100 °C delivers 2-aryl-1,2-dihydrophthalazines with yields ranging from 60 to 91%. The transformation is considered to proceed as an intermolecular condensation/intramolecular nucleophilic substitution.

Reaction of 1-nitroso-2-naphthols with α-functionalized ketones and related compounds: the unexpected formation of decarbonylated 2-substituted naphtho[1,2-d][1,3]oxazoles.

Reactions between 1-nitroso-2-naphthols and α-functionalized ketones such as α-bromo-, α-chloro-, α-mesyloxy-, α-tosyloxy-, and α-hydroxy ketones under basic conditions delivered 2-substituted naphtho[1,2-d][1,3]oxazoles in a single synthetic operation. The product formation was accompanied by the unexpected loss of the C═O group from the α-functionalized ketones. With aryl bromides, allyl bromides, α-bromo diketones, α-bromo cyanides, α-bromoesters, and α-bromo ketoesters as substrates the formation of naphtho[1,2-d][1,3]oxazoles was also observed.

Cu-catalyzed reaction of 1,2-dihalobenzenes with 1,3-cyclohexanediones for the synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones.

The Cu(I)-catalyzed reaction of 1-bromo-2-iodobenzenes and other 1,2-dihalobenzenes with 1,3-cyclohexanediones in DMF at 130 °C using Cs(2)CO(3) as a base and pivalic acid as an additive selectively delivers 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones with yields ranging from 47 to 83%. The highly regioselective domino process is based on an intermolecular Ullmann-type C-arylation followed by an intramolecular Ullmann-type O-arylation. Substituted products are accessible by employing substituted 1-bromo-2-iodobenzenes and substituted 1,3-cyclohexanediones as substrates.