The Chemistry of Benzotriazole Derivatives: A Tribute to by Jean-Christophe M. Monbaliu

By Jean-Christophe M. Monbaliu

The sequence themes in Heterocyclic Chemistry provides serious reports on current and destiny tendencies within the learn of heterocyclic compounds. total the scope is to hide subject matters facing all parts inside of heterocyclic chemistry, either experimental and theoretical, of curiosity to the overall heterocyclic chemistry neighborhood. The sequence comprises subject comparable volumes edited through popular editors with contributions of specialists within the box. All chapters from subject matters in Heterocyclic Chemistry are released on-line First with a person DOI. In references, subject matters in Heterocyclic Chemistry is abbreviated as best Heterocycl Chem and mentioned as a journal.

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Alkoxy/aryloxymethyl-1H-benzotriazole derivatives are primarily used as synthetic equivalents of acetal anions for one-carbon homologations of aldehydes and for the preparation of ethers. Their unique set of properties makes them useful synthons for the preparation of ketones, alkynes, (thio)acylsilanes, and acyltrifluoroborates. Their anions are considered as carbenoid species [217]. 1 Preparation of 1H-Benzotriazole-1-methanol The preparation of 1H-benzotriazole-1-methanol (2c), also known as 1-hydroxymethylbenzotriazole, is straightforward and was originally reported in 1952 by Hall and coworkers (Scheme 40) [164].

1g -78 °C, 1 h, then rt 1 h X = O, S, NTs R = H, alkyl, aryl 62 30-66% R = H, 4-Br, 2-Cl, 3,4-(CH3O)2, aryl R X CN 63 16-71% CN 1. LDA or n-BuLi R1 CN R 2. 1g 0 °C to rt, 12 h (b) (c) 1. LDA, THF, 0 °C, 15 min R2 R1 R2 R1 = alkyl, benzyl, aryl R2 = CN, CO2Me, COMe, COPh, SO2Ph, aryl, alkyl 2. 1g 35-78% Scheme 28 (a) Electrophilic cyanation of arylacetonitrile anions; (b) cyanation of substituted thiophenes and pyrroles; (c) cyanation of activated methylene groups OMOM OMOM 1. s-BuLi, THF, -78 °C, 2 h (a) NC 2.

Bischoff’s procedure was then utilized by various research groups including Nicolaou [219], Shishido [220], Marcaurelle [221], and many others [222–232] for the hydroxymethylation of complex substrates. For instance, a key hydroxymethylation step with 2c was utilized for the total syntheses of Myceliothermophins C, D, and E (Scheme 41b) [219], Aspermytin A 105 (Scheme 41c) [220], Cycloclavine scaffolds (Scheme 41d) [226], and various terpenoid tridecane skeletons 110 (Scheme 41e) [227]. The other important synthetic facet of 2c is its use as a Mannich electrophile, generally under acidic conditions, which triggers the release of a reactive iminium species.

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