- nBu4NI-catalyzed direct amination of benzoxazoles with tertiary amines using TBHP as oxidant under microwave irradiation
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A facile, efficient, and practical method for nBu4NI-catalyzed direct C-H amination of benzoxazoles with tertiary amines has been developed. The system could be performed in the absence of metal catalyst and only requires tert-butyl
- Yuan, Jin-Wei,Jin, Ming,Yin, Qiu-Yue,Mao, Pu,Qu, Ling-Bo
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p. 317 - 325
(2016/04/26)
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- Copper-catalyzed direct amination of benzoxazoles using primary amines as nitrogen sources
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A facile, efficient, and simple protocol for direct oxidative C-H amination of benzoxazoles with primary amines through copper-catalyzed C-H bond activation using tert-butyl peroxide (TBP) as oxidant under air has been developed. The reaction proceeds smoothly at ambient temperature to furnish the products. A variety of substituted aminobenzoxazoles were synthesized with good to excellent yields.
- Gu, Jian,Cai, Chun
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supporting information
p. 639 - 642
(2015/03/14)
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- Chloroformamidinium salts: Efficient reagents for preparation of 2-aminobenzoimidazole, 2-aminobenzoxazole, and 2-aminobenzothiazole derivatives
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A Reaction involving chloroformamidinium salts (TCFH 1a, BTCFH 1b, DmCFH 1c, DmPCFH 1d, BPCFH 1e) and 2-aminophenol 9a, benzene-1,2-diamine 9b, and 2-aminothiophenol 9c afforded 2-aminobenzoxazole 13, 2-aminobenzoimidazole 14, and 2-aminobenzothiazole 15 derivatives, respectively as major products, due to the in situ heterocyclization with dimethylamine acting as the better leaving group. Attempts for preparation of 13-15 from the reaction of N,N-dimethyl carbomyl chloride 16 with 2-aminophenol 9a, benzene-1,2-diamine 9b, and 2-aminothiophenol 9c were unsuccessful, and gave the unexpected products benzoxazol-2-ol 18a, benzoimidazol-2-one 18b, and S-(2-amino-phenyl) N,N-dimethylthiocarbamate 19 respectively. On the other hand reaction of chloroformamidinium salts 1a-e with 3-benzyl-2-hydrazinoquinoxaline 3 and 1-hydrazinophthalazine hydrochloride 4 in the presence of triethylamine as a base, afforded the [1,2,4]triazolo derivatives 6 and 7 respectively in good yield and purity. These triazole derivatives were formed due to the strong tendency towards heterocyclization and substitution of dimethylamine group as a better leaving group.
- El-Faham, Ayman,Chebbo, Mohamed,Abdul-Ghani, Mohamed,Younes, Ghassan
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p. 599 - 606
(2007/10/03)
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- Selectivity in the Consecutive SNAr-Dequaternization Reactions of Heteroaromatic Chlorides with Tertiary Amines under High Pressure
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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
- Matsumoto, Kiyoshi,Toda, Mitsuo,Hashimoto, Shiro
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p. 1283 - 1286
(2007/10/02)
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