138282-12-9

Upstream product

• 14235-81-5 4-Ethynylaniline 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 7702-38-7 N-(4-bromophenyl)benzamide 

Downstream Products

• 5411-13-2 N-(4-acetylphenyl)benzamide 
• 10278-46-3 N-(4-cyanophenyl)benzamide 

Relevant academic research and scientific papers

Assembly of BF4-, PF6-, ClO4- and F- with trinuclear copper(i) acetylide complexes bearing amide groups: structural diversity, photophysics and anion binding properties

Trinuclear copper(i) acetylide complexes 1·BF4-4·BF4, 1·PF6, 1·ClO4 and 4·F have been synthesized and characterized. Five kinds of discrete or polymeric structures could be found in their crystal structures. Among them, complexes 1·BF4, 1·PF6, and 1·ClO4 form zigzag one-dimensional (1D) anion coordination polymers (ACPs) using anions as nodes and cations 1 as ligands. For complex 2·BF4, hydrogen bonds between adjacent amide groups afford the zigzag 1D polymeric chains, which are supported by the interaction between dppms and anions. A 1D infinite meso-helical hydrogen bonding polymeric chain with a counter anion bound in each cation can be observed in complex 3·BF4. Complex 4·BF4 is unable to form polymeric chains, while complex 4·F that exhibits similar structure with 4·BF4 could construct infinite 1D polymer via hydrogen bonds between amide groups. The photophysical properties of copper(i) acetylide complexes have been studied. They show luminescence both in the solid state and DMSO solution at 298 K. The anion binding abilities of complexes 1·BF4-4·BF4 in DMSO have also been studied by using 1H NMR and UV-vis titration experiments. Their dramatic color change towards F- in DMSO enables naked eye detection of F-.

A model chiral graft copolymer demonstrates evidence of the transmission of stereochemical information from the side chain to the main chain on a nanometer scale

A model chiral graft copolymer, poly(phenylacetylene)-g-poly(n-hexyl isocyanate) (PPA-g-PHIC), in which a chiral moiety is located at the end of each PHIC side chain, was synthesized. First, chiral PHIC macromonomers with a phenylacetylene end group were synthesized via living anionic polymerization using the functional initiator sodium N-(4-ethynylphenyl)benzamide (Na-4EPBA) and then end-capped using the chiral terminator (S)-2-acetoxypropionyl chloride ((S)-Ct). The molecular weights (MWs) of the PHIC macromonomers were controlled based on the feed ratio of the monomer to the initiator. Subsequent polymerization of PHIC macromonomers using Rh+(2,5-norbornadiene) [(η6-C6H5)B-(C6H 5)3] (Rh(nbd)BPh4) catalyst generated chiral PPA-g-PHIC graft copolymers with varying graft strand lengths. Chiral macromonomers and graft copolymers were characterized by SEC-MALLS, NMR, and CD spectroscopy. This model chiral graft copolymer provided an excellent example of the transmission of stereochemical information from the side chain to the main chain, as a preferred helicity was induced in the PPA backbone of the graft copolymer even when chiral moieties were separated from the main chain by nanometer scale distances (5.4-13 nm). Furthermore, CD spectroscopy clearly showed that the CD intensity of the PPA main chain was directly dependent on the CD intensity of the optically active PHIC side chain determined by the strand length.

PdCl2-catalyzed synthesis of a new class of isocoumarin derivatives containing aminosulfonyl / aminocarboxamide moiety: First identification of a isocoumarin based PDE4 inhibitor

While anti-inflammatory properties of isocoumarins are known their PDE4 inhibitory potential was not explored previously. In our effort the non-PDE4 inhibitor isocoumarins were transformed into the promising inhibitors via introducing an aminosulfonyl/aminocarboxamide moiety to the C-3 benzene ring attached to the isocoumarin framework. This new class of isocoumarins were synthesized via a PdCl2-catalyzed construction of the 4-allyl substituted 3-aryl isocoumarin ring starting from the appropriate 2-alkynyl benzamide derivative. Several compounds showed good inhibition of PDE4B in vitro and the SAR indicated superiority of aminosulfonamide moiety over aminocarboxamide in terms of PDE4B inhibition. Two compounds 3q and 3u with PDE4B IC50 = 0.43 ± 0.11 and 0.54 ± 0.19 μM and ≥ 2-fold selectivity over PDE4D emerged as initial hits. The participation of aminosulfonamide moiety in PDE4B inhibition and the reason for selectivity though moderate shown by 3q and 3u was revealed by the in silico docking studies. In view of potential usefulness of moderately selective PDE4B inhibitors the compound 3u (that showed PDE4 selectivity over other PDEs) was further evaluated in adjuvant induced arthritic rats. At an intraperitoneal dose of 30 mg/kg the compound showed a significant reduction in paw swelling (in a dose dependent manner), inflammation and pannus formation (in the knee joints) as well as pro-inflammatory gene expression/mRNA levels and increase in body weight. Moreover, besides its TNF-α inhibition and no significant toxicity in an MTT assay the compound did not show any adverse effects in a thorough toxicity studies e.g. teratogenicity, hepatotoxicity, cardiotoxicity and apoptosis in zebrafish. Thus, the isocoumarin 3u emerged as a new, safe and moderately selective PDE4B inhibitor could be useful for inflammatory diseases possibly including COVID-19.

Sulfur–Fluoride Exchange (SuFEx)-Mediated Synthesis of Sterically Hindered and Electron-Deficient Secondary and Tertiary Amides via Acyl Fluoride Intermediates

Amide bond formation is one of the most executed reactions in chemistry and biology. This is largely due to the ubiquity of the amide functional group in biological molecules, natural products and pharmaceutically important drugs. We report here the development of “SuFExAmide”: a new sulfur–fluoride exchange (SuFEx) click chemistry based protocol for the efficient amidation of carboxylic acids via acyl fluoride intermediates. We have developed benzene-1,3-disulfonyl fluoride as a cost effective, powerful and versatile coupling agent, which delivers challenging secondary and tertiary amides in excellent yields from sterically hindered and electron-deficient amines. The straightforward method offers significant benefits over existing protocols in terms of substrate scope, efficiency and ease of operation and is demonstrated by the synthesis of 44 amides, including GNF6702, an antiprotozoal drug candidate. In the majority of cases, the amide products are obtained in high yield without the need for excess reagents or chromatographic purification.

Catalyst-free hydrochlorination protocol for terminal arylalkynes with hydrogen chloride

We present a simple and straightforward protocol for hydrochlorination of terminal arylalkynes to vinyl chlorides using hydrogen chloride under mild reaction conditions. This protocol does not involve any metal catalysts or additives. It is simple, inexpensive, and easy to prepare, and exhibits good reaction activity. The hydrochlorination proceeds smoothly to yield unique regioselective products via the Markovnikov addition rule.

Aerobic oxynitration of alkynes with tBuONO and TEMPO

An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.