2364-57-0Relevant articles and documents
Total synthesis of diazaquinomycins H and J using double Knorr cyclization in the presence of triisopropylsilane
Prior, Allan M.,Sun, Dianqing
, p. 1759 - 1771 (2019/01/26)
The first total synthesis of diazaquinomycins H (1) and J (2), which are promising anti-tuberculosis natural product leads, has been achieved via selective amidation of diamine 6 with Meldrum's acid derivatives, subsequent EDC coupling with 3-oxobutanoic
Scope and Optimization of the Double Knorr Cyclization: Synthesis of Novel Symmetrical and Unsymmetrical Tricyclic 1,8-Diazaanthraquinones
Prior, Allan M.,Sun, Dianqing
, p. 859 - 871 (2018/02/10)
The Knorr cyclization of β-ketoanilides to form 2-quinolones in the presence of acid is well documented chemistry. Double Knorr cyclization is rare, with very few examples appearing in the literature to date. The double Knorr methodology can provide access to tricyclic 1,8-diazaanthraquinones, a scaffold seen in the diazaquinomycin family. The optimized synthesis of diazaquinomycin A and structural analogues thereof via double Knorr cyclization of di-β-ketoanilide precursor substrates is reported. The scope and generality of the double Knorr cyclization were investigated along with an optimization study. The double Knorr cyclization was found to be sensitive to steric bulk on precursor substrates. In addition, the presence of a 5-hydroxy group on the 1,3-di-β-ketoanilide facilitated the double Knorr cyclization, possibly due to its stabilizing effect on the carbocation intermediates formed during the reaction.
The Power of Packing: Metallization of an Organic Semiconductor
Mailman, Aaron,Leitch, Alicea A.,Yong, Wenjun,Steven, Eden,Winter, Stephen M.,Claridge, Robert C. M.,Assoud, Abdeljalil,Tse, John S.,Desgreniers, Serge,Secco, Richard A.,Oakley, Richard T.
supporting information, p. 2180 - 2183 (2017/02/23)
Benzoquino-bis-1,2,3-dithiazole 5 is a closed shell, antiaromatic 16π-electron zwitterion with a small HOMO-LUMO gap. Its crystal structure consists of planar ribbon-like molecular arrays packed into offset layers to generate a "brick-wall" motif with str
Total synthesis of lavendamycin by a [2+2+2] cycloaddition
Nissen, Felix,Detert, Heiner
experimental part, p. 2845 - 2853 (2011/06/26)
The total synthesis of the bacterial-derived, pentacyclic, antitumor antibiotic lavendamycin has been achieved through a highly convergent strategy. The key step of this synthesis is a ruthenium-catalyzed [2+2+2] cycloaddition of an electron-deficient nit
