3844-54-0Relevant articles and documents
Direct Deamination of Primary Amines via Isodiazene Intermediates
Berger, Kathleen J.,Driscoll, Julia L.,Yuan, Mingbin,Dherange, Balu D.,Gutierrez, Osvaldo,Levin, Mark D.
supporting information, p. 17366 - 17373 (2021/11/04)
We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.
Synthesis and bioactivity of novel 3-(1-hydroxyethylidene)-5-substituted- pyrrolidine-2,4-dione derivatives
Han, Bao Feng,Shi, Qing Ming,Wang, Xian Feng,Liu, Jian Bo,Qiang, Sheng,Yang, Chun Long
experimental part, p. 1023 - 1026 (2012/10/08)
Ten novel 5-substituted derivatives of 3-(1-hydroxyethylidene)pyrrolidine- 2,4-dione were synthesized. The compounds were confirmed by IR, 1H NMR, MS and elemental analysis. The bioassay indicated that these compounds showed noticeable herbicid
Tandem multi-step synthesis of C-carboxyazlactones promoted by N-heterocyclic carbenes
Campbell, Craig D.,Duguet, Nicolas,Gallagher, Katherine A.,Thomson, Jennifer E.,Lindsay, Anita G.,O'Donoghue, AnnMarie C.,Smith, Andrew D.
supporting information; body text, p. 3528 - 3530 (2009/02/05)
Cascade reaction sequences incorporating N-heterocyclic carbene-based organocatalysis have been developed that allow the direct preparation of a range of (±)-4-phenoxycarbonylazlactones in good isolated yields (66-84%) from the corresponding N-p-anisoyl amino acids. The Royal Society of Chemistry.