DMSO/t-BuONa/O2-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles was written by Yang, Ruchun;Yue, Shusheng;Tan, Wei;Xie, Yongfa;Cai, Hu. And the article was included in Journal of Organic Chemistry in 2020.Formula: C8H6N2O2 This article mentions the following:
Aromatic N-heterocycles such as quinolines I [R1 = H, 8-Cl, 6-OMe, etc.; R2 = H, 3-Me, 4-Ph, etc. X = N; Y = CH2], isoquinolines I [R1 = H; R2 = H, 1-Ph; X = CH2; Y = N] and indoles II [R1 = H, 5-F, 4-Br, etc.; R2 = H, 2-Me; Y = CH2, N] were synthesized via a sodium tert-butoxide promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution This reaction proceeded under mild reaction conditions with a good functional group tolerance. Mechanistic studies suggested a radical pathway involved hydrogen abstraction of dimsyl radicals from the N-H bond or 伪-C-H of the substrates, and subsequent oxidation of the nitrogen or 伪-aminoalkyl radicals. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).
6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C8H6N2O2
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles