69218-56-0

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 5638, 1995 DOI: 10.1021/jo00122a053

Upstream product

• 683-57-8 bromo-acetic acid amide 
• 15217-42-2 sodium benzotriazolate 
• 872-85-5 pyridine-4-carbaldehyde 
• 111198-08-4 1-(cyanomethyl)benzotriazole 

Downstream Products

• 853261-81-1 2-[4-(2-furyl)-2-pyridon-6-yl]benzoic acid 
• 853261-82-2 2-[4-(2-thienyl)-2-pyridon-6-yl]benzoic acid 
• 853261-74-2 2-[4-(4-chlorophenyl)-2-pyridon-6-yl]benzoic acid 
• 853261-80-0 2-[4-(3-methoxyphenyl)-2-pyridon-6-yl]benzoic acid 
• 853261-79-7 2-[4-(4-methoxyphenyl)-2-pyridon-6-yl]benzoic acid 
• 853261-78-6 2-[4-(2-chlorophenyl)-2-pyridon-6-yl]benzoic acid 
• 853261-71-9 2-[4-(4-methylphenyl)-2-pyridon-6-yl]benzoic acid 
• 853261-72-0 2-[4-(4-isopropylphenyl)-2-pyridon-6-yl]benzoic acid 
• 853261-55-9 2-(4-phenyl-2-pyridon-6-yl)benzoic acid 
• 853261-73-1 2-[4-(4-fluorophenyl)-2-pyridon-6-yl]benzoic acid 
• 1086627-05-5 2-fluoro-5-(6-{2-[(2-methylpropyl)oxy]phenyl}-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile 
• 1086626-19-8 4-(3-methyl-1H-indazol-5-yl)-6-{2-[(2-methylpropyl)oxy]phenyl}pyridin-2(1H)-one 
• 931112-45-7 6-(5-chloro-2-hydroxyphenyl)-4-(2-chloro-5-(trifluoromethyl)phenyl)-2(1H)-pyridinone 
• 168697-98-1 N-Phenyl-α-(benzotriazol-1-yl)-4-phenylthiazol-2-acetamide 

Relevant academic research and scientific papers

Synthesis of E/Z 3-(1H-benzotriazol-1-YL)-3-(pyridin-4- YL)acrylonitriles and E/Z 2-(3-imino-2-benzofuran-1(3H)- Ylidene)acetonitriles. An unusual case of displacement of the benzotriazole ring

Synthesis of 3-(1H-benzotriazol-1-yl)-3-(pyridin-4-yl)acrylonitriles (E/Z 6) and 2-(3-imino-2-benzofuran-1(3H)-ylidene)acetonitriles (E/Z 20), by an unusual case of displacement of the benzotriazole ring, has been described. The X-Ray structure analysis of Z 20 and antimycobacterial activity of both E/Z 6 and E/Z 20 were also reported.

Benzotriazole-Assisted Preparations of 2-(Substituted amino)pyridines and Pyrid-2-ones

Base-promoted reactions of benzotriazolyl-containing acetic acid derivatives, 2-(benzotriazol-1-yl)acetonitrile (7a), 2-(benzotriazol-1-yl)acetamide (7b), and (±)-2-(benzotriazol-1-yl)propionamide (7c), with α,β-unsaturated ketones 8 give efficient and regioselective access to previously difficult to attain 3-unsubstituted pyridine derivatives: the 2-(substituted amino)pyridines 14a-k and the 4,6-substituted pyrid-2-ones 15a-h. The pyridine rings result from tandem [3 + 3] annulations involving a Michael addition followed by cyclization.

1-(cyanomethyl)benzotriazole as a convenient precursor for the synthesis of 2-substituted thiazoles

Treatment of 1-(cyanomethyl)benzotriazole with hydrogen peroxide followed by a Lawesson reagent afforded (benzotriazol-1-yl)thioacetamide which condensed with α-halo carbonyl compounds (Hantzsch thiazole synthesis) to give the corresponding 2-(benzotriazol-1-ylmethyl)thiazoles. Lithiation of 2-(benzotriazol-1-ylmethyl)-4-phenylthiazole with butyllithium occurred exclusively at the methylene group, and subsequent quenching of the resulting anion with alkyl halides produced the corresponding alkylated products in good yields. Treatment of these intermediates with Grignard reagents in toluene or with electron-rich heterocycles in the presence of zinc bromide resulted in the displacement of benzotriazole to afford the corresponding thiazoles with elaborated 2-substituents.