156136-84-4Relevant academic research and scientific papers
Diversity-oriented synthesis of bicyclic fragments containing privileged azines
Luise, Nicola,Wyatt, Paul G.
, p. 248 - 251 (2019)
An innovative and efficient reagent- and scaffold-based diversity oriented synthesis (DOS) of a fragment set was developed for fragment-based drug discovery (FBDD) programs. Twelve diverse, functionalized and bicyclic scaffolds were rapidly accessed by adopting a convenient synthetic toolkit around three privileged azine cores in order to effectively modulate biomolecules. These structures are characterized by both key motifs for interacting with diverse biological targets via hydrogen bonds and useful points of growth for subsequent fragment optimization.
1,3-dipolar cycloaddition of hydrazones with α-oxo-ketenes: A three-component stereoselective entry to pyrazolidinones and an original class of spirooxindoles
Presset, Marc,Mohanan, Kishor,Hamann, Marie,Coquerel, Yoann,Rodriguez, Jean
supporting information; experimental part, p. 4124 - 4127 (2011/10/04)
Stereodefined monocyclic, spirobicyclic, and bis-spirotricyclic pyrazolidin-3-ones can be prepared efficiently by a three-component reaction involving a 1,3-dipolar cycloaddition of azomethine imines obtained from hydrazones with α-oxo-ketene dipolarophiles generated in situ. The reaction allows the creation of four covalent bonds and two contiguous chiral quaternary centers with excellent diastereoselectivity in a single catalyst/additive-free, highly atom-economical transformation. From a fundamental point of view, the reaction introduces α-oxo-ketenes as effective dipolarophiles in 1,3-dipolar cycloadditions.
LITHIATION ROUTES TO OXINDOLES AND 2-INDOLINETHIONES: PRECURSORS TO 2,2'-DITHIOBISINDOLES WITH TYROSINE KINASE INHIBITORY PROPERTIES
Rewcastle, Gordon W.,Denny, William A.
, p. 701 - 708 (2007/10/02)
N-Substituted oxindoles and 2-indolinethiones can be prepared by lithiation of carboxyl protected N,2-dimethylanilines followed by quenching with CO2 or CS2 respectively. 2-Indolinethione derivatives are also available via demethylation of 2-methylthioindoles, which are prepared by lithiation of N-substituted indoles and treatment with dimethyl disulfide.
