78072-94-3

Upstream product

• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 100-61-8 N-methylaniline 
• 1843-21-6 N-phenyl-2-benzothiazolamine 
• 77-78-1 dimethyl sulfate 
• 121-69-7 N,N-dimethyl-aniline 
• 136-95-8 2-amino-benzthiazole 
• 95-16-9 1,3-Benzothiazole 
• 615-22-5 2-methylmercaptobenzothiazole 
• 116928-25-7 benzo[d]thiazol-2-yltriphenylphosphonium trifluoromethanesulfonate 

Downstream Products

• 100726-34-9 benzothiazol-2-yl-methyl-(4-nitroso-phenyl)-amine 

Relevant academic research and scientific papers

C-H Functionalization of Benzothiazoles via Thiazol-2-yl-phosphonium Intermediates

Benzothiazoles undergo regioselective C2-H functionalization with triphenylphosphine to form thiazol-2-yl-triphenylphosphonium salts, and these phosphonium salts react with a wide range of O- A nd N-centered nucleophiles to give the corresponding ethers, amines, and C-N biaryls. The reactions proceed under mild conditions and allow for the recovery of triphenylphosphine at the end of the sequence. In the presence of hydroxide, phosphonium salts undergo disproportionation, resulting in the reduction of the benzothiazole, which is useful for specific C2 deuteration of benzothiazoles.

Pd-PEPPSI-IPentAn Promoted Deactivated Amination of Aryl Chlorides with Amines under Aerobic Conditions

We report herein a highly efficient Pd-catalyzed amination by "bulky-yet-flexible" Pd-PEPPSI-IPentAn complexes. The relationship between the N-heterocyclic carbenes (NHCs) structure and catalytic properties was discussed. Sterically hindered (hetero)aryl chlorides and a variety of aliphatic and aromatic amines can be applied in this cross-coupling, which smoothly proceeded to provide desired products. The operationally simple protocol highlights the rapid access to CAr-N bond formation under mild conditions without the exclusion of air and moisture.

Copper-catalyzed synthesis of 2-aminobenzothiazoles from 2-iodophenyl isocyanides, potassium sulfide and amines

A simple and practically useful synthetic method for the synthesis of a variety of 2-aminobenzothiazoles was developed. This methodology could construct one C-N bond and two C-S bonds in a step reaction and provide the desired products in good to perfect yields.

Palladium-catalyzed amination of aryl sulfides with aliphatic amines

Conditions for the palladium-NHC-catalyzed amination of aryl sulfides with aliphatic as well as aromatic amines were established. The KHMDS-mediated amination of heteroaryl sulfides could proceed without palladium. Based on the distinct difference in reactivity of C-Br and C-S bonds, a sequential amination of bromothioanisole can take place to install two different alkylamino groups onto the aromatic ring in one pot. A palladium-NHC precatalyst shows high efficiency for C-S bond cleavage for the amination of aryl sulfides with aliphatic amines or aromatic amines.

Cu(acac)2 catalyzed oxidative C-H bond amination of azoles with amines under base-free conditions

This work reports a simple and efficient methodology for oxidative C-H bond amination of azoles with aromatic/aliphatic amines using copper-bis- acetylacetonate complex catalyst. The catalyst works very well in the absence of external acid or base and requires only molecular oxygen as an oxidant. The methodology is applicable for the oxidative C-H bond amination of various azoles with different types of aromatic/aliphatic amines for the synthesis of various aminoheterocycles with good to excellent yields.

Copper-catalyzed oxidative C-H, N-H coupling of azoles and thiophenes

CH, NH coupling of azole and thiophene derivatives takes place in the presence of a catalytic amount of Cu(OAc)2 and an additive. The reaction of azoles smoothly occurs with several amines and amides catalyzed by 20 mol % of Cu(OAc)2-2PPh3 and 4 equiv of NaOAc under O2 or in the presence of Ag2CO3 under N 2. The coupling reaction leads to a facile synthesis of a N-substituted analogue of 2,5-diarylthiazole, which shows photoluminescent properties with extended π-conjugation. Spectroscopic characteristics of the obtained thiazole derivatives are discussed by measurements of UV-vis absorption and photoluminescent spectra. Under the reaction conditions using Ag 2CO3 as an additive and Cu(OAc)2-2PPh 3 as a catalyst, thiophene derivatives also react with 2-pyrrolidone to undergo CH, NH amidation.

Direct amination of azoles via catalytic C-H, N-H Coupling

C-H, N-H Coupling of azoles takes place with several amines in the presence of a copper catalyst to undergo amination at the 2-position. The reaction of benzothiazole with N-methylaniline in the presence of sodium acetate and 20 mol % Cu(0Ac)2

Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides

Detailed studies have been conducted to determine the activity of palladium catalysts for the amination of five-membered heterocyclic halides and to determine the factors that control the scope of this reaction. Palladium-catalyzed aminations of the electron-rich furanyl, thiophenyl, and indolyl halides and of the related 2-halogenated thiazoles, benzimidazole, and benzoxazole have been shown to occur with a subset of amines. Various combinations of palladium precursors and PtBu3 were tested as catalysts for reaction of 3-bromothiophene with N-methylaniline, and the fastest reactions occurred with the Pd(I) dimer, [PdBr(PtBu3)]2. The fastest aminations of thiazoles, benzimidazoles, and benzoxazoles occurred with the combination of palladium trifluoroacetate and PtBu3 as catalyst.

Unexpected dealkylation during nucleophilic substitution: Synthesis of 2-N,N-dialkylamino benzoxazoles and benzothiazoles

Mild reaction conditions are described for the preparation of a number of 2-alkyl- and 2-arylaminobenzoxazoles and benzothiazoles from 2-chlorobenzoxazole and 2-chlorobenzothiazole and N-methyl or other simple N-alkyl tertiary amines. The reaction proceeds neat or in THF solution and involves dealkylation of the amine reactant by nucleophilic substitution by chloride. In the case of N-methylpyrrolidine and N-methylpiperidine demethylation was not observed and the major product was formed by ring opening to give chlorobutyl- and chloropentyl-methylamino substituted benzoxazoles and benzothiazoles. Treatment of the chlorobutyl derivative with iodide in acetone afforded the new 1H,2H,3H,4H,5H-[1,3]diazepino[2,1-b][1,3]benzoxazol-6-ium ring system. (C) 2000 Elsevier Science Ltd.

Selectivity in the Consecutive SNAr-Dequaternization Reactions of Heteroaromatic Chlorides with Tertiary Amines under High Pressure

Consecutive SNAr-dealkylation reactions of heteroaromatic chlorides such as 2-chloro-5-trifluoromethylpyridine and 2-chlorobenzothiazole with tertiary amines took place under high pressure in a highly selective fashion; some synthetic potential