52372-78-8Relevant articles and documents
Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketonesviaN2H4mediated deoxygenative couplings
Lv, Leiyang,Li, Chao-Jun
, p. 2870 - 2875 (2021/03/14)
Umpolung (polarity reversal) tactics of aldehydes/ketones have greatly broadened carbonyl chemistry by enabling transformations with electrophilic reagents and deoxygenative functionalizations. Herein, we report the first ruthenium-catalyzed β-selective alkylation of vinylpyridines with both naturally abundant aromatic and aliphatic aldehyde/ketonesviaN2H4mediated deoxygenative couplings. Compared with one-electron umpolung of carbonyls to alcohols, this two-electron umpolung strategy realized reductive deoxygenation targets, which were not only applicable to the regioselective alkylation of a broad range of 2/4-alkene substituted pyridines, but also amenable to challenging 3-vinyl and steric-embedded internal pyridines as well as their analogous heterocyclic structures.
Synthesis, in-vitro and in-silico studies of triazinoindole bearing bis-Schiff base as β-glucuronidase inhibitors
Ahmad, Shakeel,Aziz, Aamir,Khan, Fahad,Rahim, Fazal,Sarfraz, Maliha,Taha, Muhammad,Ullah, Hayat,Wadood, Abdul
, (2021/07/16)
Triazinoindole bearing bis-Schiff base analogs (1–20) were synthesized by triazinoindole-thione ring formation, triazinoindole-thiol-phenylethanone, followed by triazinoindole bis-Schiff base formation. Synthesized analogs showed β-glucuronidase potential with IC50 value ranging between 2.60 ± 0.10 to 55.40 ± 1.60 μM as compared to standard D-saccharic acid 1,4-lactone (IC50 = 48.10 ± 1.2 μM). Analog 20 was the most potent one with IC50 value 2.60 ± 0.10 μM. Analogs 17, 4 showed IC50 values 5.20 ± 0.20 and 5.70 ± 0.20 μM respectively and withstand 2nd and 3rd ranked scaffolds among the synthesized analogs. All other sixteen analogs showed many-fold better potency with IC50 values ranging from 7.9 ± 0.2 to 48.1 ± 1.2 μM. The structure-activity relationship was established and confirmed of binding interactions through molecular docking studies.
Switch in Selectivity for Formal Hydroalkylation of 1,3-Dienes and Enynes with Simple Hydrazones
Li, Chao-Jun,Lv, Leiyang,Qiu, Zihang,Yu, Lin
supporting information, p. 6466 - 6472 (2020/03/13)
Controlling reaction selectivity is a permanent pursuit for chemists. Regioselective catalysis, which exploits and/or overcomes innate steric and electronic bias to deliver diverse regio-enriched products from the same starting materials, represents a powerful tool for divergent synthesis. Recently, the 1,2-Markovnikov hydroalkylation of 1,3-dienes with simple hydrazones was reported to generate branched allylic compounds when a nickel catalyst was used. As part of the effort, shown here is that a complete switch of Markovnikov to anti-Markovnikov addition is obtained by changing to a ruthenium catalyst, thus providing direct and efficient access to homoallylic products exclusively. Isotopic substitution experiments indicate that no reversible hydro-metallation across the metal-π-allyl system occurred under ruthenium catalysis. Moreover, this protocol is applicable to the regiospecific hydroalkylation of the distal C=C bond of 1,3-enynes.
