77414-69-8Relevant academic research and scientific papers
Arylation of amines and monoarylation of symmetrical diamines in the presence of brine solution with diheteroaryl halides
Verma, Sanjeev K.,Ghorpade, Ramarao,Kaushik
supporting information, p. 2645 - 2655 (2014/08/18)
A simple, scalable, ligand-free, and metal-free protocol for arylation of amines and monoarylation of symmetrical diamines with diheteroaryl halides in the presence of brine solution has been developed. The protocol has broad structural applicability for chemoselective monoarylation of a wide variety of symmetrical, cyclic, and acyclic aliphatic diamines. The protocol is also applicable for selective arylation of aliphatic amine in the presence of aromatic amine.
Novel solid-phase parallel synthesis of N-substituted-2-aminobenzo [d]thiazole derivatives via cyclization reactions of 2-iodophenyl thiourea intermediate resin
Kim, Seul-Gi,Jung, Se-Lin,Lee, Gee-Hyung,Gong, Young-Dae
, p. 29 - 40 (2013/03/13)
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).
A DBU-diheteroaryl halide adduct as the fastest current N-diheteroarylating agent
Verma, Sanjeev K.,Acharya,Ghorpade, Ramarao,Pratap, Ajay,Kaushik
, p. 18783 - 18786 (2013/10/22)
An unexpected diazabicyclo[5.4.0]undec-7-ene (DBU) catalysed rate enhancement of N-arylation of amines with diheteroaryl halides is reported. DBU is found to activate the Ar-Cl bond of a diheteroaryl halide, forming a green coloured adduct under neat conditions. The activated green coloured adduct was used for the arylation of amines under neat conditions and was found to be the fastest diheteroarylating agent reported to date. The Royal Society of Chemistry 2013.
Palladium(II) acetate as catalyst for the N-alkylation of aromatic amines, sulfonamides, and related nitrogenated compounds with alcohols by a hydrogen autotransfer process
Martinez-Asencio, Ana,Yus, Miguel,Ramon, Diego J.
experimental part, p. 3730 - 3740 (2011/12/21)
Palladium(II) acetate is a versatile, inexpensive, and simple catalyst for the selective N-monoalkylation of amino derivatives with poor nucleophilic character, such as aromatic and heteroaromatic amines as well as carboxamides, sulfonamides, and phosphazenes, using, in all cases, primary alcohols as the initial source of the electrophile, through a hydrogen autotransfer process. The regioselectivity of the benzothiazol-2-amine alkylation is contrary to that found using halogenated electrophiles.
Chemospecific and ligand free CuI catalysed heterogeneous N-arylation of amines with diheteroaryl halides at room temperature
Verma, Sanjeev K.,Acharya,Kaushik
supporting information; experimental part, p. 1324 - 1327 (2011/04/16)
A ligand free, copper-catalyzed N-arylation reaction of amines with diheteroaryl halides in heterogeneous medium at room temperature has been developed. The protocol is very effective for low boiling amines and useful for amines available in aqueous solution. The reaction gives chemospecific arylation of amines with diheteroaryl halides in the mixture monoheteroaryl halides, diheteroaryl halides and carbocyclic aryl halides. The reaction is also chemospecific with respect to arylation of aliphatic amines. Monoarylated piperazines were also synthesized at room temperature following this protocol. The Royal Society of Chemistry 2011.
