- A general synthesis of 1-(1-alkenyl)benzotriazoles
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1-Methyl, 1-(alkoxymethyl) and 1-(trimethylsilylmethyl)benzotriazoles are metallated at the α-carbon. Trapping of the resulting metallated species with chlorotrimethylsilane gives compounds which undergo Peterson olefination even with hindered ketones. In some cases, metallation at the 4-position of the benzotriazole is observed. An exhaustive metallation/silylation sequence gives 4-trimethylsilyl substituted 1-benzotriazoles in good yields.
- Pleynet, David P.M.,Dutton, Jonathan K.,Johnson, Peter A.
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p. 11903 - 11926
(2007/10/03)
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- (Benzotriazol-1-yl)methoxymethyl anion: A novel methylal anion equivalent
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The title anion readily reacts with a variety of electrophiles to give adducts which, upon treatment with methanol in the presence of p-toluenesulfonic acid, afford the corresponding α-functionalized dimethyl acetals.
- Katritzky,Yang,Cundy
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p. 3061 - 3071
(2007/10/02)
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- Reactions of 1-(α-Alkoxyalkyl)- and 1-(α-(Aryloxy)alkyl)benzotriazoles with the Grignard Reagents. A New and Versatile Method for the Preparation of Ethers
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1-(α-Alkoxyalkyl)benzotriazoles deriving from aldehydes (other than formaldehyde), or from ketones, react with Grignard reagents at 110 deg C to provide a high-yielding, general synthesis of dialkyl and aryl ethers.Under similar conditions, 1-(alkoxymethyl)- and 1-((aryloxy)methyl)benzotriazoles give, by a different cleavage pattern of the N-C-O grouping, 1-alkylbenzotriazoles and N,N'-dialkyl-o-phenylenediamines.The 1-(α-alkoxyalkyl)benzotriazoles are easily prepared: (a) by condensation of benzotriazole, an aldehyde, and an alcohol under water-removing conditions; (b) by condensation of a 1-(α-chloroalkyl)benzotriazole with a sodium or potassium alkoxide or aryloxide; and (c) by condensatioon of an acetal or a ketal with benzotriazole.All the 1-(α-alkoxyalkyl)benzotriazoles and dialkyl or alkyl aryl ethers obtained were fully characterized by their 1H and 13C NMR spectra.
- Katritzky, Alan R.,Rachwal, Stanislaw,Rachwal, Bogumila
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p. 6022 - 6029
(2007/10/02)
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- The Chemistry of N-Substituted Benzotriazoles. Part 2. Reactions of Benzotriazole with Aldehydes and Aldehyde Derivatives. 1-(α-Hydroxyalky)-, 1-(α-Alkoxyalkyl)-, and 1-(α-Acyloxyalkyl)benzotriazoles
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Benzotriazole reacts readily with a variety of aldehydes to yield crystalline 1:1 adducts characterized by strong hydrogen bonding.Corresponding 1-(α-alkoxyalkyl)benzotriazoles are formed in the presence of alcohols, and 1-(α-acetoxyalkyl) analogues resul
- Katritzky, Alan R.,Rachwal, Stanislaw,Rachwal, Bogumila
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p. 791 - 798
(2007/10/02)
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