10166-08-2Relevant articles and documents
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Kitching,W. et al.
, p. 4643 - 4648 (1975)
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Regioselective, Diastereoselective, and Enantioselective One-Pot Tandem Reaction Based on an in Situ Formed Reductant: Preparation of 2,3-Disubstituted 1,5-Benzodiazepine
Yang, Gao-Feng,Li, Guang-Xun,Huang, Jin,Fu, Ding-Qiang,Nie, Xiao-Kang,Cui, Xin,Zhao, Jin-Zhong,Tang, Zhuo
, p. 5110 - 5119 (2021)
The 1,5-benzodiazepines are important skeletons frequently contained in medicinal chemistry. Herein, we described an unexpected tandem cyclization/transfer hydrogenation reaction for obtaining chiral 2,3-disubstituted 1,5-benzodiazepines. The enolizable aryl aldehydes were chosen as substrates to react with symmetric and unsymmetric o-phenylenediamines. The unforeseen tandem reaction occurred among many possible latent side reactions under chiral phosphoric acid catalysis and affords the corresponding products in moderate yields and regioselectivities, good diastereoselectivities, and enantiomeric ratio (up to 99:1).
Ring Expansion of Epoxides under Br?nsted Base Catalysis: Formal [3+2] Cycloaddition of β,γ-Epoxy Esters with Imines Providing 2,4,5-Trisubstituted 1,3-Oxazolidines
Kondoh, Azusa,Odaira, Kenta,Terada, Masahiro
, p. 11240 - 11244 (2015)
A novel ring-expansion reaction of epoxides under Br?nsted base catalysis was developed. The formal [3+2] cycloaddition reaction of β,γ-epoxy esters with imines proceeds in the presence of triazabicyclodecene (TBD) as a superior Br?nsted base catalyst to afford 2,4,5-trisubstituted 1,3-oxazolidines in a highly diastereoselective manner. This reaction involves the ring opening of the epoxides with the aid of the Br?nsted base catalyst to generate α,β-unsaturated esters having an alkoxide at the allylic position, which would formally serve as a synthetic equivalent of the 1,3-dipole, followed by a cycloaddition reaction with imines in a stepwise fashion. This methodology enables the facile synthesis of enantioenriched 1,3-oxazolidines from easily accessible enantioenriched epoxides.
Selective switchable iron-catalyzed hydrosilylation of carboxylic acids
Misal Castro, Luis C.,Li, Haoquan,Sortais, Jean-Baptiste,Darcel, Christophe
, p. 10514 - 10516,3 (2012)
Selective reduction of carboxylic acids either to aldehydes or alcohols is achieved using a one pot procedure based on iron-catalyzed hydrosilylations. Using phenylsilane and (COD)Fe(CO)3 catalyst under UV-irradiation at rt, alcohols were obtained specifically in good yields, whereas aldehydes were selectively obtained using TMDS and (t-PBO)Fe(CO)3 catalyst under thermal activation.
Microwave-Assisted oxidation reaction of primary alcohols with sensitive functional groups to aldehydes using Ruthenium Diphosphorus Complexes
Marimuthu, Thashree,Alapour, Saba,Friedrich, Holger B.
, p. 120 - 135 (2020/10/30)
Microwave-assisted oxidation of primary alcohols to aldehydes is described using complexes with bidentate diphosphorus-xanthene ligands coordinated to Ru. The reactions took place readily at 120°C with 1 mol% catalyst loading that was generated in situ from the added [Ru(H)2(PPh3)3(CO)] and diphosphine ligands. The aldehyde yields for the benzylic alcohols were in the range 50-100%, while aliphatic alcohols gave yields of 48- 74%. For the first time, oxidation reactions under solvent-free conditions using these ligands are also presented, making the reaction greener. Other metals were also tested, and it was found that changing the metal center to Ir, Rh, or Os results in complexes that showed minimal or no activity towards the desired product.
Copper-Catalyzed Ring-Opening/Reconstruction of Anthranils with Oxo-Compounds: Synthesis of Quinoline Derivatives
Zou, Liang-Hua,Zhu, Hao,Zhu, Shuai,Shi, Kai,Yan, Cheng,Li, Ping-Gui
, p. 12301 - 12313 (2019/10/11)
A copper-catalyzed protocol for the construction of various 2-aryl(alkyl)-3-acylquinolines or 3-arylquinolines using readily available anthranils and 1,3-diketones or aldehydes as starting materials is reported herein. Dioxygen as the sole oxidant and hexafluoroisopropanol as the solvent play an important role in both procedures. This ring-opening/reconstruction strategy involving N-O bond cleavage and C-N/C-C bond formation features high yields and broad substrate scope.