Methyl Azaarenes Research Articles

Iron-catalyzed C(sp3)–H functionalization of methyl azaarenes with α-oxoesters: a facile approach to lactic acid derivatives

A highly efficient method for the C(sp3)–H functionalization of methyl azaarenes to α-oxoesters in the presence of iron(II) acetate as an inexpensive, nontoxic catalyst with moderate-to-excellent yields has been developed. This transformation represents a facile approach to medicinally important lactic acid derivatives.

Iron-catalyzed C(sp3)–H functionalization of methyl azaarenes: a green approach to azaarene-substituted α- or β-hydroxy carboxylic derivatives and 2-alkenylazaarenes

An iron-catalyzed C(sp3)–H functionalization of methyl azaarenes with carbonyls to access the title compounds have been described.

Microwave assisted water mediated benzylic C–H functionalization of methyl aza-arenes and nucleophilic addition to aromatic aldehydes

Abstract A highly efficient method is described for the sp 3 C–H bond functionalization of methyl aza-arenes in the presence of water under microwave irradiation and subsequent addition to aromatic aldehydes. This transformation represents an efficient way to synthesize 2-alkyl aza-arene derivatives from simple starting materials.

Brønsted acid catalyzed synthesis of 1,3-di(2-quinolyl)propane derivatives via tandem C(sp3)–H functionalization

A novel protocol for Brønsted acid catalyzed reaction of 2-methyl azaarenes and aromatic aldehyde to give 1,3-di(2-quinolyl)propane derivatives through tandem C(sp3)–H bond functionalization has been developed. This approach provides a new access to a variety of 1,3-di(2-quinolyl)propane derivatives, which are potentially of great importance in pharmaceuticals and ligand fields.

ChemInform Abstract: Lewis Acid Catalyzed Csp3—H Functionalization of Methyl Azaarenes with α‐Trifluoromethyl Carbonyl Compounds.

AbstractYtterbium triflate is found to be highly efficient for the title reaction, delivering trifluormethylated alcohols in excellent yields.

A novel and efficient synthesis of azaarene-substituted 3-hydroxy-2-oxindoles via sp3 C–H functionalization of 2-methyl azaarenes and (2-azaaryl)methanes over a heterogeneous, reusable silica-supported dodecatungstophosphoric acid catalyst

A novel and efficient protocol has been developed for the synthesis of azaarene-substituted 3-hydroxy-2-oxindoles via sp3 C–H functionalization of 2-methyl azaarenes and (2-azaaryl)methanes with isatin in good to excellent yield. This is the first example in which heterogeneous, reusable silica supported dodecatungstophosphoric acid (DTP/SiO2) catalyzed sp3 C–H functionalization of 2-substituted azaarenes and (2-azaaryl)methanes.

Lewis acid-catalyzed Csp3–H functionalization of methyl azaarenes with α-trifluoromethyl carbonyl compounds

A Lewis acid promoted Csp3–H bond functionalization of methyl azaarenes with α-trifluoromethylated carbonyl compounds is described. Catalytic amounts of Yb(OTf)3 provided a straightforward access to the corresponding trifluoromethylated alcohols in excellent yields up to 94% under mild reaction conditions.

Yb(OTf)3-Catalyzed Addition of 2-Methyl Azaarenes to Isatins via C-H Functionalization

3-Substituted-3-hydroxy-2-oxindoles are rich in a range of biologically active natural products and pharmaceuticals and development of efficient methods to construct this key motif is of vital importance. Yb(OTf)3-catalyzed addition of 2- or 4-methyl azaarenes to isatins via C-H functionalization was developed. Moderate to good yields were obtained for various isatins and azaarenes. This method provides rapid protocol for the synthesis of biologically important azaarene-substituted 3-hydroxy-2-oxindoles in one step. The success of this reaction expands the synthetic utility of Lewis acid in the catalytic functionalization of sp3 C-H bonds in organic synthesis. 发展了 Yb(OTf)3 催化的碳氢键活化 2-甲基氮杂芳烃或 4-甲基氮杂芳烃对靛红的加成反应, 对不同靛红和氮杂芳烃都取得了较好的产率. 该方法能够一步快速合成具有重要生理活性的氮杂芳烃取代的 3-羟基-2-氧化吲哚类化合物, 同时该反应成功扩展了路易斯酸在 sp3 碳氢键活化中的应用.

Facile Synthesis of Azaarene-Substituted 3-Hydroxy-2-oxindoles via Brønsted Acid Catalyzed sp3 C–H Functionalization

Brønsted acid catalyzed functionalization of sp(3) C-H bonds in 2-methyl azaarenes has been achieved in the reaction with isatins. This method provides facile synthesis of biologically important azaarene-substituted 3-hydroxy-2-oxindoles in one step in moderate to good yields.

Highly efficient vinylaromatics generation via iron-catalyzed sp3 C–H bond functionalization CDC reaction: a novel approach to preparing substituted benzo[α]phenazines

An iron-catalyzed benzylic vinylation was developed to transfer the carbon atom in the N,N-dimethyl moiety of N,N-dimethylacetamide (or N,N-dimethylformamide) to 2-methyl azaarenes to generate 2-vinyl azaarenes.

Palladium-Catalyzed Benzylic Addition of 2-Methyl Azaarenes to N-Sulfonyl Aldimines via C−H Bond Activation

An efficient protocol for the generation of amines by palladium-catalyzed nucleophilic benzylic addition of 2-methyl-substituted azaarenes to N-sulfonyl aldimines under neutral conditions via C-H bond activation has been developed. This reaction represents a very efficient methodology for the synthesis of heterocycle-containing amines and thus opens a new way to access amines through C-H bond activation.