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Upstream product

• 136-95-8 2-amino-benzthiazole 
• 122-01-0 4-chloro-benzoyl chloride 
• 74-11-3 para-chlorobenzoic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 69791-46-4 N-(benzo[d]thiazol-2-yl)-1-(4-chlorophenyl)methanimine 
• 16794-67-5 p-chlorobenzoyl isothiocyanate 
• 637-87-6 1-Chloro-4-iodobenzene 
• 201230-82-2 carbon monoxide 

Relevant academic research and scientific papers

A novel gold(I)-mediated intramolecular transamidation of benzoyl thiourea derivatives to form benzamides via dethiocyanation

A novel gold(I)-mediated intramolecular transamidation of thiourea derivatives to yield benzamides via dethiocyanation have been achieved by the reaction of 3-(1,3-benzothiazol-2-yl)-1-(benzoyl)thiourea derivatives in the presence of gold(I) precursors. The compounds have been characterized using IR, NMR, GC-MS and microanalysis. The single crystal XRD of 3-(1,3-benzothiazol-2-yl)-1-(3-bromobenzoyl)thiourea (5), 3-(1,3-benzothiazol-2-yl)-1-(3-methoxybenzoyl)thiourea (6), N-(benzothiazol-2-yl)benzamide (10), N-(benzothiazol-2-yl)-3-chlorobenzamide (11), N-(benzothiazol-2-yl)-4-nitrobenzamide (12), N-(benzothiazol-2-yl)-3-bromobenzamide (14) have been discussed. The novel transformation is thought to proceed by a gold(I)-mediated intramolecular transamidation reaction which releases thiocyanate to yield the benzamide. Density functional theory calculations have been used to support the proposed mechanism for this transformation.

Synthesis of benzamide-benzothiazole conjugates via palladium-catalysed aminocarbonylation (hydrazinocarbonylation)

The palladium-catalysed aminocarbonylation of iodoarenes was investigated using 2-amino- and 2-hydrazinobenzothiazole as N-nucleophile. The reaction proved to be highly chemoselective in all cases: carboxamides and the corresponding carbohydrazides, obtained by the acylation at the nitrogen adjacent to the C-2 of the benzothiazole moiety, were obtained exclusively and isolated in moderate to high yields. Systematic investigation of the reaction conditions revealed that the reaction requires relatively high temperature (higher than 70 °C). The effect of the carbon monoxide pressure is different in the synthesis of the two types of products: while the carboxamide formation is favoured, the carbohydrazide formation is lowered by the increasing CO pressure.

Access to Amide from Aldimine via Aerobic Oxidative Carbene Catalysis and LiCl as Cooperative Lewis Acid

Herein, an efficient route to amides from aldimines via aza-Breslow intermediates through aerobic oxidative carbene catalysis with LiCl as a cooperative Lewis acid is described. Many of the obtained N-heteroarylamides feature biological activity. Ambient

Facile synthesis of N-acyl 2-aminobenzothiazoles by NHC-catalyzed direct oxidative amidation of aldehydes

A mild, general, and high yielding synthesis of N-acyl 2-aminobenzothiazoles has been demonstrated by N-heterocyclic carbene (NHC)-organocatalyzed direct amidation of aldehydes with 2-aminobenzothiazoles proceeding via acyl azolium intermediates. The carbene generated from the triazolium salt under oxidative conditions was the key for the success of this reaction. The method was subsequently applied to the synthesis of various biologically important N-acyl 2-aminobenzothiazoles.

Imidazolium-supported benzotriazole: an efficient and recoverable activating reagent for amide, ester and thioester bond formation in water

An efficient and recyclable imidazolium-supported benzotriazole reagent (Im-CH2-BtH) as a novel synthetic auxiliary has been synthesized and its utility as a carboxyl group activating reagent via the formation of stable imidazolium-supported acyl benzotriazoles was explored for the synthesis of amides, esters and thioesters in water under microwave conditions. The reagent was reused five times without any noticeable loss in activity. It is moisture insensitive and highly stable under thermal and aerobic conditions. The application of imidazolium-supported N-acetyl benzotriazole leads to synthesis of paracetamol on the gram scale under greener conditions in 93% yield.

Novel solid-phase parallel synthesis of N-substituted-2-aminobenzo [d]thiazole derivatives via cyclization reactions of 2-iodophenyl thiourea intermediate resin

A novel solid-phase methodology has been developed for the synthesis of N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo[d]thiazole resins 5 by cyclization reaction of 2-iodophenyl thiourea resin 3. The resin-bound 2-iodophenyl thiourea 3 is produced by addition of 2-iodophenyl isothiocyanate 2 to the amine-terminated linker amide resin 1. These core skeleton 2-aminobenzo[d]thiazole resins 5 undergo functionalization reactions with various electrophiles, such as alkyl halides, acid chlorides, and sulfonyl chlorides to generate N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole resins 6, 7, and 8, respectively. Finally, N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives 9, 10, and 11 are then generated in good yields and purities by cleavage of the respective resins 6, 7, and 8 using trifluoroacetic acid (TFA) in dichloromethane (DCM).

Metallic bismuth and aluminium: New and efficient catalysts for the preparation of various amides

A new and efficient method for the preparation of various amides has been achieved by a simple reaction of an acid chloride with primary and secondary amines in the presence of bismuth or aluminium powder in anhydrous toluene.

Zinc mediated facile amide formation : Application to alkyl, aryl, heterocycle, carbohydrate and amino acids

Synthesis of alkyl, aryl, heterocyclic, carbohydrate and amino acid amides using activated zinc is described. The recovery and reuse of the zinc makes the procedure more economic.

CORRELATION OF STRUCTURAL PARAMETERS WITH ANTITUBERCULOTIC ACTIVITY IN A GROUP OF 2-BENZAMIDOBENZOTHIAZOLES

Fourteen 2-benzamidobenzothiazole derivatives substituted in the benzoyl group and 2-cinnamamidobenzothiazole have been synthetized.The prediction of active structures by the method by Topliss gives incorrect results but, as shown on the basis of the Hans