70286-37-2Relevant academic research and scientific papers
A Short Total Synthesis of Benzophenanthridine Alkaloids via a Rhodium(III)-Catalyzed C-H Ring-Opening Reaction
Aravindan, Narasingan,Jeganmohan, Masilamani
, p. 14826 - 14843 (2021/10/20)
The biologically important naturally available benzophenanthridines were prepared efficiently in three steps with overall good yields. A new synthetic methodology involving a rhodium(III) catalyzed redox-neutral ring-opening of 7-azabenzonorbornadienes with aromatic aldoximes is developed to synthesize the target molecules. The developed C-H ring-opening reaction is highly diastereoselective and compatible with various sensitive functional group substituted aromatic aldoximes as well as substituted 7-azabenzonorbornadienes. The ring-opening products were transformed into highly sensitive 13,14-dehydrobenzo phenanthridine derivatives by HCl hydrolysis. Subsequently, 13,14-dehydrobenzophenanthridines were converted into biologically important benzophenanthridine alkaloids in the presence of DDQ. A possible reaction mechanism was proposed for the C-H ring-opening reaction and supported by the deuterium labeling studies.
Cyclic Hydroxamic Acid Analogues of Bacterial Siderophores as Iron-Complexing Agents prepared through the Castagnoli–Cushman Reaction of Unprotected Oximes
Bakulina, Olga,Bannykh, Anton,Dar'in, Dmitry,Krasavin, Mikhail
supporting information, p. 17667 - 17673 (2017/12/26)
The first application of multicomponent chemistry (the Castagnoli–Cushman reaction) toward the convenient one-step preparation of cyclic hydroxamic acids is described. Cyclic hydroxamic acids are close analogues of bacterial siderophores (iron-binding com
One-pot synthesis of alternating peptides exploiting a new polymerization technique based on Ugi's 4CC reaction
Koyama, Yasuhito,Gudeangadi, Prashant G.
supporting information, p. 3846 - 3849 (2017/04/04)
We developed a one-pot synthetic technique for alternating peptides. Central to this technique is a new, catalyst-free polymerization based on Ugi's 4CC reaction. The treatment of imines with the ambident molecules bearing both an isocyanide and a carboxylic acid afforded alternating peptides.
Regiospecific synthesis of substituted 2-nitrobenzaldehydes from benzaldehydes through palladium-catalyzed chelation-assisted C-H nitration
Zhang, Wei,Wu, Degui,Zhang, Jian,Liu, Yunkui
, p. 5827 - 5835 (2014/10/15)
A regiospecific synthesis of substituted 2-nitrobenzaldehydes from substituted benzaldehydes has been developed that involves a three-step process with palladium-catalyzed chelation-assisted C-H nitration as the key step. In the process, O-methyl aldoxime serves as a removable directing group for the palladium-catalyzed ortho-nitration of substituted benzaldoximes and it can be removed in subsequent conversion of the resulting 2-nitrobenzaldoximes into 2-nitrobenzaldehydes.
Solid-phase synthesis of benzothiazoles using an alkoxyamine linker
Hioki, Hideaki,Matsushita, Kimihito,Noda, Takeshi,Yamaguchi, Kota,Kubo, Miwa,Harada, Kenichi,Fukuyama, Yoshiyasu
scheme or table, p. 4337 - 4342 (2012/09/25)
An alkoxyamine linker was applied for the solid-phase synthesis of benzothiazoles. The substrate was anchored by aldoxime linkage and products were cleaved from the solid-support by aldoxime-imine exchange coupled with air-oxidation under the weakly acidi
Ruthenium-catalysed conversion of oxime ethers into nitriles
Anand, Naveen,Owston, Nathan A.,Parker, Alexandra J.,Slatford, Paul A.,Williams, Jonathan M.J.
, p. 7761 - 7763 (2008/02/12)
The conversion of oxime ethers into nitriles has been achieved under neutral conditions using Ru(CO)(PPh3)3H2 and the bidentate ligand Xantphos as the catalyst.
HIV Integrase inhibitors
-
, (2008/06/13)
The present invention relates to the inhibition of HIV integrase, and to the treatment of AIDS or ARC by administering compounds of the following formula, or a tautomer of said compound, or a pharmaceutically acceptable salt, solvate or prodrug thereof: wherein R1, R2 and B1 are as defined herein.
Inhibition of the antibacterial target UDP-(3-O-acyl)-N-acetylglucosamine deacetylase (LpxC): Isoxazoline zinc amidase inhibitors bearing diverse metal binding groups
Pirrung, Michael C.,Tumey, L. Nathan,Raetz, Christian R. H.,Jackman, Jane E.,Snehalatha, Karnem,McClerren, Amanda L.,Fierke, Carol A.,Gantt, Stephanie L.,Rusche, Kristin M.
, p. 4359 - 4370 (2007/10/03)
UDP-3-O-[R-3-hydroxymyristoyl]-GlcNAc deacetylase (LpxC) is a zinc amidase that catalyzes the second step of lipid A biosynthesis in Gram negative bacteria. Known inhibitors of this enzyme are oxazolines incorporating a hydroxamic acid at the 4-position,
Tandem oxidation processes: The direct conversion of activated alcohols into oximes; synthesis of citaldoxime
Kanno, Hisashi,Taylor, Richard J. K.
, p. 1287 - 1290 (2007/10/03)
The direct conversion of primary alcohols into oximes is reported using manganese dioxide and alkoxylamines/hydroxylamine as their hydrochloride salts or supported on Amberlyst 15. This transformation has been applied to a range of benzylic, allylic and propargylic alcohols and utilised to prepare the natural product citaldoxime.
