75690-78-7

Upstream product

• 2205-01-8 N-methoxyphenethylamine 
• 98-03-3 thiophene-2-carbaldehyde 
• 64-04-0 phenethylamine 
• 82649-27-2 1,3-dioxoisoindolin-2-yl thiophene-2-carboxylate 
• 636-72-6 2-thiophenemethanol 
• 1590361-11-7 O-diethylcarbamoyl-N-phenethylhydroxylamine 
• 88372-95-6 thiophen-2-yl(trimethylsilyl)methanone 
• 1590361-20-8 N-tert-butoxycarbonyl-O-diethylcarbamoyl-N-phenethylhydroxylamine 
• 103-63-9 1-phenyl-2-bromoethane 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 100-42-5 styrene 
• 5813-89-8 2-thiophenylcarboxamide 
• 527-72-0 2-thiophenylcarboxylic acid 

Downstream Products

• 96460-67-2 5-phenyl-2-(thiophene-2-yl)oxazole 
• 120086-35-3 1-(2-thienyl)-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions

We report the facile amide-forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high-yielding and displays excellent functional-group tolerance. Late-stage modifications of an array of marketed drugs, peptides, natural products, and biologically active compounds showcase the robustness and functional-group tolerance of the reaction. The key to the success of the reaction could be the possible formation of the strong Si?O bond via a Brook-type rearrangement. Given its simplicity and efficiency, this ligation has the potential to unfold new applications in the areas of medicinal chemistry and chemical biology.

Visible Light-Driven Efficient Synthesis of Amides from Alcohols using Cu?N?TiO2 Heterogeneous Photocatalyst

Amides were synthesized from alcohols and amines in high yields using an in situ generated active ester of N-hydroxyimide with our developed Cu?N?TiO2 catalyst at room temperature using oxygen as a sole oxidant under visible light. The catalyst can be easily prepared, robust, and recycled four times without a considerable change in catalytic activity. This developed protocol applies to a wide substrate scope and has good functional group tolerance. The application of this amidation reaction has been successfully demonstrated for the synthesis of moclobemide, an antidepressant drug, and an analog of the itopride drug on a gram scale.

Base-Mediated Anti-Markovnikov Hydroamidation of Vinyl Arenes with Arylamides

We investigated a base-promoted protocol for the intermolecular anti-Markovnikov hydroamidation of vinyl arenes with arylamides to furnish the arylethylbenzamides with excellent chemo- and regioselectivity. The reaction tolerates an extensive variety of functional groups and has been successfully extended with electronically varied handles, aminobenzamides, electron-rich/electron-deficient heterocyclic amides, and vinyl arenes to afford the hydroamidated products. Excellent chemoselectivity was observed for the amide group over amine. The proposed mechanism and vital role of the solvent was well supported by deuterium labeling studies and control experiments.

Direct Amidation of Carboxylic Acids through an Active α-Acyl Enol Ester Intermediate

The development of a highly efficient and simple protocol for the direct amidation of carboxylic acids is described employing ynoates as novel coupling reagents. The transformation proceeds in good to excellent yields via in situ α-acyl enol ester intermediates formation under mild reaction conditions. This useful method has been demonstrated for a range of substrates to provide a succinct access to structurally diverse amides, including key intermediates of glibenclamide, tiapride hydrochloride, and nateglinide, and can be conducted on a mole scale.

Direct oxidative amidation of aldehydes with amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions via a dual-catalysis process

A simple and efficient procedure for the synthesis of amides directly from aldehydes and amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions has been reported. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media, and operational simplicity are the main highlights. The proposed dual-catalysis mechanistic pathway was briefly investigated. Furthermore, the heteropolyanion-based ionic liquids were easily reusable for this oxidative amidation.

CuCl/TBHP catalyzed synthesis of amides from aldehydes and amines in water

A CuCl/TBHP catalyzed amidation of aldehydes with amine under aqueous media is described. Both aliphatic and aromatic aldehydes coupled with a variety of amines under the reaction conditions employed.

Synthesis and antifungal activity evaluation of new heterocycle containing amide derivatives

A series of heterocycle containing amide derivatives (1-28) were synthesised by the combination of acyl chlorides (1a, 2a) and heterocyclic/homocyclic ring containing amines, and their in vitro antifungal activity was evaluated against five plant pathogenic fungi, namely Gibberella zeae, Helminthosporium maydis, Rhizoctonia solani, Botrytis cinerea and Sclerotinia sclerotiorum. Results of antifungal activity analysis indicated that some of the products showed good to excellent antifungal activity, as compound 2 showed excellent activity against G. zeae and R. solani and potent activity against H. maydi, B. cinerea and S. sclerotiorum, and compounds 1, 8 and 10 also displayed excellent antifungal potential against H. maydi, B. cinerea and S. sclerotiorum and good activity against R. solani when compared with the standard carbendazim.

Synthesis and chemoselective ligations of MIDA acylboronates with O-Me hydroxylamines

N-Methyliminodiacetyl (MIDA) acylboronates undergo chemoselective amide-bond forming ligations in water with O-Me hydroxylamines, including unprotected peptide substrates. These bench-stable boronates were easily prepared from potassium acyltrifluoroborat

Efficient procedure for the preparation of amides using polymer-bound reagents

An effective method for the conversion of acids into amides is presented. The two-step procedure includes the preparation of acid chloride intermediates using Pol-Ph3P and subsequent treatment of these intermediates with amines and polymer-bound base. The amides were accessible in high yields and purities without further purification.