135085-79-9Relevant academic research and scientific papers
C-H Functionalization of Benzothiazoles via Thiazol-2-yl-phosphonium Intermediates
Sch?mberg, Fritz,Vilotijevic, Ivan,Wagner, Konrad,Zi, You
supporting information, (2020/05/05)
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.
Copper-catalyzed oxidative C-H, N-H coupling of azoles and thiophenes
Mitsuda, Shinobu,Fujiwara, Taiki,Kimigafukuro, Katsuyoshi,Monguchi, Daiki,Mori, Atsunori
scheme or table, p. 3585 - 3590 (2012/06/30)
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
Monguchi, Daiki,Fujiwara, Taiki,Furukawa, Hirotoshi,Mori, Atsunori
supporting information; experimental part, p. 1607 - 1610 (2009/09/06)
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
Photochemical Synthesis of 2-Substituted Benzothiazoles
Muthusamy, Sengoden,Paramasivam, Rangasamy,Ramakrishnan, Vayalakkavoor T.
, p. 759 - 763 (2007/10/02)
The photochemical reaction of 1-indolethiocarbanilides 1, di- and tri-substituted thioureas 3-5 and 4,4-dimethyl-2,6-dioxothiocyclohexanecarboxanilides 9 affording the respective benzothiazoles are described.
