38301-07-4Relevant academic research and scientific papers
Divergent and facile Lewis acid-mediated synthesis of N-alkyl 2-aminomethylene-1,3-indanediones and 2-alkylamino-1,4-naphthoquinones
Zhang, Qian,Chang, Cheng-Wei Tom
, p. 893 - 896 (2015)
N-Alkyl 2-aminomethylene-1,3-indanediones and 2-alkylamino-1,4-naphthoquinones are known for their diverse and versatile bioactivities and applications. Traditionally, these two compounds were synthesized in separate routes using different materials. By e
Divergent synthesis of three classes of aryl N-glycosides by solvent control
Zhang, Jianjun,Chang, Cheng-Wei Tom
experimental part, p. 685 - 695 (2009/06/28)
Aryl glycosides represent a group of molecules with immense biological applications and implications. While the syntheses of aryl C-glycosides and O-glycosides have been studied extensively, the preparation for aryl N-glycosides is relatively unexplored. By employing 1,4-naphthoquinone and glycosyl azides undergoing a [3 + 2] cycloaddition, we have developed a convenient method for constructing three different classes of aryl N-glycosides that include N-glycosylated 2-aminomethylene-1,3-indanedione, benzazepine-1,5-dione, and 9,10-anthraquinone derivatives via solvent control. It was found that conducting cycloaddition in DMF formed exclusively 9,10-anthraquinone derivatives, while less polar solvent such as toluene offered all three aryl N-glycosides. The synthesis of N-glycosylated 9,10-anthraquinone derivatives is of particular interest since no known example has been documented. The synthesis of these N-glycosylated heterocyclic compounds using traditional glycosylation methods could be challenging. Therefore, our diversity-oriented protocols can be viewed as an alternative and practical glycosylation approach. In addition, we have also demonstrated that alkyl azides can also undergo the same cycloaddition, further expanding the structural repertoire available for a broader interest. Initial anticancer assays have revealed that 19f and 19k exert mean growth percent of 17.58 and-5.95, respectively.
Lewis Acid-Mediated Reactions of Alkyl Azides with α,β- Unsaturated Ketones
Reddy, D. Srinivasa,Judd, Weston R.,Aube, Jeffrey
, p. 3899 - 3902 (2007/10/03)
(Matrix presented) Alkyl azides react with saturated ketones upon treatment with Lewis acids to afford ring-expansion products through the azido-Schmidt reaction, but this reaction does not proceed when α,β-unsaturated ketones are used. In this study, alk
