61555-85-9

Upstream product

• 106-49-0 p-toluidine 
• 135-02-4 ortho-anisaldehyde 
• 612-16-8 (2-methoxyphenyl)methanol 

Downstream Products

• 1587696-55-6 4-(2-methoxyphenyl)-3,3-dimethyl-1-(4-methylphenyl)azetidin-2-one 
• 1578258-28-2 2,5-bis(2-methoxyphenyl)-1,4-bis(4-methylphenyl)-1,4-dihydropyrrolo[3,2-b]pyrrole 
• 130191-24-1 N-(2-methoxybenzyl)-4-methylaniline 

Relevant academic research and scientific papers

Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction

In the course of synthesizing and testing various "azole-including" cyclic anhydrides in the Castagnoli-Cushman reaction with imines, a remarkably reactive, pyrrole-based anhydride has been identified. It displayed a remarkably efficient reaction with N-alkyl and N-aryl imines, in particular, with "enolizable" α-C-H imines which typically fail to react with a majority of known cyclic anhydrides. The reactivity of this anhydride has been justified by an efficient resonance stabilization of its enol form. This finding expands the existing arsenal of highly reactive cyclic anhydrides and further confirms the importance of anhydride enolization for an efficient Castagnoli-Cushman reaction.

Tetraaryl-, pentaaryl-, and hexaaryl-1,4-dihydropyrrolo[3,2- b ]pyrroles: Synthesis and optical properties

Efficient conditions for the synthesis of tetra-, penta-, and hexasubstituted derivatives of 1,4-dihydropyrrolo[3,2-b]pyrrole were developed. The tetraaryl derivatives were obtained in a novel one-pot reaction among aromatic aldehydes, aromatic amines, and butane-2,3-dione. After a thorough examination of various reaction parameters (solvent, acid, temperature) p-toluenesulfonic acid was identified as the crucial catalyst. As a result, 1,4-dihydropyrrolo[3,2-b]pyrroles were obtained in the highest yields reported to date. The scope and limitation studies showed that this new method was particularly efficient for sterically hindered aldehydes (yields 45-49%). Pentaaryl- and hexaaryl-1,4-dihydropyrrolo[3,2-b]pyrroles were prepared from tetraaryl-1,4-dihydropyrrolo[3,2-b]pyrroles via direct arylation by employing both electron-poor and electron-rich aromatic and heteroaromatic haloarenes. Strategic placement of electron-withdrawing substituents at the 2-, 3-, 5-, and 6-positions produced an acceptor-donor-acceptor type fluorophore. The resulting multiply substituted heteropentalenes displayed intriguing optical properties. The relationship between the structure and photophysical properties for all compounds were directly compared and thoroughly elucidated. All synthesized products displayed strong blue fluorescence and exhibited moderate to large Stokes shifts (3000-7300 cm-1) as well as high quantum yields of fluorescence up to 88%. Two-photon absorption cross-section values measured in the near-IR region were surprisingly high (hundreds of GM), given the limited conjugation in these propeller-shaped dyes.

Dehydrogenation and oxidative coupling of alcohol and amines catalyzed by organosilicon-supported TiO2@PMHSIPN

The catalytic dehydrogenation and tandem transformation of aromatic alcohols, including oxidative coupling of alcohols and amines, were achieved successfully using a catalytic amount of organosilicon-supported titania (TiO2@PMHSIPN), which enables the efficient synthesis of aromatic aldehydes, imines, and benzimidazoles in good to excellent yields. This journal is the Partner Organisations 2014.