Studies on mesoionic compounds. Part 10. Synthesis and chemical properties of mesoionic 1,2,5-thiadiazolium-3-olates
作者:Katsutada Masuda、Jun Adachi、Keiichi Nomura
DOI:10.1039/p19810001033
日期:——
The preparation of a novel mesoionic heterocycle is described; derivatives of 4-aryl-5-alkyl-1,2,5-thiadiazolium-3-olates (6a–f) are obtained by treatment of α-N-substituted aminophenylacetamides with sulphur monochloride followed by base.
Free-Radical Version of the Strecker Synthesis of α-Aminoamides Promoted by Aqueous H<sub>2</sub>O<sub>2</sub>/TiCl<sub>3</sub>/HCONH<sub>2</sub> System
作者:Rosalba Cannella、Angelo Clerici、Walter Panzeri、Nadia Pastori、Carlo Punta、Ombretta Porta
DOI:10.1021/ja061092g
日期:2006.4.1
A new reaction of general synthetic interest representing the free-radical version of the Strecker synthesis to alpha-aminoamides is reported. A hydroxy radical, generated by Ti(III) one-electron reduction of H2O2, abstracts a H atom from the C-H bond of formamide, and the resulting carbamoyl radical adds to the C atom of aldimines formed in situ, leading to a one-pot synthesis of alpha-aminoamides
报道了代表 Strecker 合成的自由基版本对 α-氨基酰胺的普遍合成兴趣的新反应。由 Ti(III) 对 H2O2 进行单电子还原产生的羟基自由基从甲酰胺的 CH 键中提取一个 H 原子,所得氨基甲酰基自由基与原位形成的醛亚胺的 C 原子相加,形成一锅法α-氨基酰胺的合成。几种类型的醛可以参与该过程。
MASUDA KATSUTADA; ADACHI JUN; NOMURA KEIICHI, J. CHEM. SOC. PERKIN TRANS., PART 1, 1981, NO 4, 1033-1036