41194-02-9Relevant academic research and scientific papers
Cu(OTf)2catalyzed Ugi-type reaction ofN,O-acetals with isocyanides for the synthesis of pyrrolidinyl and piperidinyl 2-carboxamides
Feng, Yi-Man,Lin, Guo-Qiang,Mao, Zhuo-Ya,Nie, Xiao-Di,Si, Chang-Mei,Wei, Bang-Guo
supporting information, p. 9248 - 9251 (2021/09/20)
The Cu(OTf)2catalyzed Ugi-type reactions ofN,O-acetals with isocyanides have been described for the synthesis of pyrrolidinyl and piperidinyl 2-carboxamides. 4-Hydroxy-5-substituted-prolinamides can be obtained in high diastereoselectivities (2
Synthesis of 5-Substituted 2-Pyrrolidinones by Coupling of Organozinc Reagents with Cyclic N-Acyliminium Ions
Hidalgo-Mercado, Yazmín I.,Olivo, Horacio F.,Romero-Ortega, Moisés,Santos-Sánchez, Zaira A.,Zaragoza-Galicia, Ivann
, p. 4650 - 4656 (2019/12/11)
A coupling reaction between cyclic N-acyliminium ions with organozinc reagents is described. The cyclic N-acyliminium ions, generated in situ from N-substituted-5-hydroxy-2-pyrrolidinones by treatment with boron trifluoride-diethyl ether complex or titani
Metal free coupling of heteroaryl N-tosylhydrazones and thiols: Efficient synthesis of sulfides
García-Carrillo, Mario Alfredo,Guzmán, ángel,Díaz, Eduardo
supporting information, p. 1952 - 1956 (2017/04/27)
A metal free coupling of heteroaromatic N-tosylhydrazones with thiols is presented. A convenient synthetic route to synthesize heteroaryl N-tosylhydrazones is also showed. Valuable thioethers with pyrroles, pyridines, thieno[2,3-b]pyridines, imidazo[1,2-a]pyridines, and 6H-thieno[2,3-b]pyrroles derivatives were synthesized in good yields. This coupling reaction can be carried out in a one-pot fashion and scaled up to the gram scale by using heteroaryl aldehydes, without the need to isolate the N-tosylhydrazone.
Potassium Hydroxide-Catalyzed Chemoselective Reduction of Cyclic Imides with Hydrosilanes: Synthesis of ω-Hydroxylactams and Lactams
Ding, Guangni,Li, Chengjun,Shen, Yifan,Lu, Bin,Zhang, Zhaoguo,Xie, Xiaomin
, p. 1241 - 1250 (2016/04/26)
Potassium hydroxide-catalyzed hydrosilylation exhibits excellent activity and chemoselectivity for the reduction of cyclic imides under mild reaction conditions. The chemoselectivity of the reduction system may be readily tuned by changing the identity an
Zinc-catalyzed selective reduction of cyclic imides with hydrosilanes: Synthesis of ω-hydroxylactams
Ding, Guangni,Lu, Bin,Li, Yuyuan,Wan, Jun,Zhang, Zhaoguo,Xie, Xiaomin
, p. 1013 - 1021 (2015/03/30)
Cyclic imides were selectively reduced to the corresponding ω-hydroxylactams in high yields with (EtO)3SiH (triethoxysilane) or PMHS (polymethylhydrosiloxane) under catalysis of zinc diacetate dehydrate [Zn(OAc)2 2H2O] (10%) and tetramethylethylenediamine (TMEDA) (10%). This catalytic protocol showed good functional group tolerance as well as excellent regioselectivity for unsymmetrical imides bearing coordinating groups adjacent to the carbonyl.
Palladium-catalyzed C - O hydrogenolysis in γ-hydroxy γ-lactams as an efficient approach to 5-alkyl(aryl)pyrrolidin-2-ones
Turova,Berezhnaya,Starodubtseva,Ferapontov,Vinogradov
, p. 859 - 863 (2015/12/24)
5-R-Pyrrolidin-2-ones were synthesized by Pd/Sibunit-catalyzed C - O hydrogenolysis of 5-R-5-hydroxypyrrolidin-2-ones with molecular hydrogen.
Multimetallic iridium-tin (Ir-Sn3) catalyst in N-acyliminium ion chemistry: Synthesis of 3-substituted isoindolinones via intra- and intermolecular amidoalkylation reaction
Maity, Arnab Kumar,Roy, Sujit
, p. 2627 - 2642 (2014/09/30)
The multimetallic iridium-tritin (Ir-Sn3) complex [Cp*Ir(SnCl3)2{SnCl2(H2O) 2}] (1) proved to be a highly effective catalyst towards C-OH bond activation of γ-hydroxylactams, leading to a nucleophilic substitution reaction known as the α-amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer {[Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3-dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3-substituted isoindolinones and 5-substituted pyrrolidin-2-ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir-Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ-hydroxylactam towards the formation of the N-acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.
One-pot synthesis of pyrrolidino- and piperidinoquinolinones by three-component aza-Diels-Alder reactions of in situ generated N-arylimines and cyclic enamides
Zhang, Wei,Zhang, Wenxue,Dai, Yisi,Wang, Xuerui
supporting information; experimental part, p. 6122 - 6126 (2011/12/01)
An efficient synthesis of hexahydropyrrolo[3,2-c]quinolin-2-ones and hexahydropyridino[3,2-c]quinolin-2-ones has been developed in moderate to high yields by one-pot two-step aza-Diels-Alder reactions of N-arylimines, formed in situ from anilines and benz
Regioselective synthesis of 1-alkyl-5-(indol-3-yl- and -2-yl)pyrrolidin-2- ones from available reagents
Sadovoy,Kovrov,Golubeva,Sviridova
, p. 1215 - 1223 (2011/10/09)
The reaction under mild conditions of 1-alkyl-5-hydroxypyrrolidin-2-ones with different indoles having a free 3 position leads exclusively to 1-alkyl-5-(indol-3-yl)pyrrolidin-2-ones but if position 3 is occupied to 1-alkyl-5-(indol-2-yl)pyrrolidin-2-ones.
Lewis acid-promoted tandem desulfurization and hydroxylation of γ-phenylthio-substituted lactams: Novel synthetic strategy of isoindolobenzazepine alkaloid, chilenine
Yoda, Hidemi,Inoue, Kei-Ichi,Ujihara, Yasuaki,Mase, Nobuyuki,Takabe, Kunihiko
, p. 9057 - 9060 (2007/10/03)
Treatment of a variety of alicyclic and aromatic γ-phenylthio- substituted lactams with Lewis acids such as cuprous or cupric halides in aqueous solution at rt was found to undergo novel tandem desulfurization and hydroxylation reactions to generate γ-hydroxylated lactams without the ring-opened products in extremely high yields, respectively. This process was further applied to the total synthesis of an isoindolobenzazepine alkaloid, chilenine, by featuring the elaboration of the functionalized phthalimide derivative.
