2142-01-0Relevant articles and documents
Comparative study of chemically immobilized and conventional homogeneous ionic liquids as phase-transfer catalysts for the N -alkylation of heterocyclic compounds
Dogra, Shallu,Sharma, Madan L.,Singh, Jasvinder
, p. 945 - 953 (2015)
Various ionic liquids (ILs) were screened for their phase-transfer catalytic (PTC) activity using the N-alkylation of nitrogen heterocycles as the model reaction. Immobilized ILs behaved extremely well and proved to be far better catalysts than conventional homogeneous PTCs in terms of their stability, easy recovery, and reusability. The investigation also demonstrated that quaternary tetraalkylammonium salts offer very high catalytic activity, whereas aromatic heterocyclic tetravalent nitrogen catalysts (imidazolium- and pyridinium-based salts) were poorly active.
Efficient one-pot synthesis of N-substituted phthalimides/naphthalimides from azides and anhydrides by iodotrimethylsilane
Kamal, Ahmed,Laxman,Laxman,Rao, N. Venugopal
, p. 8733 - 8734 (1998)
N-Substituted phthalimides and naphthalimides have been obtained in good to excellent yields, employing chlorotrimethylsilane and sodium iodide (in situ generation of iodotrimethylsilane) from corresponding azides and anhydrides under mild conditions.
A Facile One-pot Synthesis of N-Substituted Phthalimides Using a Catalytic Amount of Crown Ether
Soai, Kenso,Ookawa, Atsuhiro,Kato, Kyoko
, p. 1671 - 1672 (1982)
N-Substituted phthalimides, intermediates of the Gabriel synthesis, were obtained in high yields (84-100percent) by the addition of a catalytic amount of 18-crown-6 to the reaction of potassium phthalimide and alkyl halides in toluene.
An Oxidation Study of Phthalimide-Derived Hydroxylactams
Adjei, Bernard L.,Luzzio, Frederick A.
, (2022/01/24)
A systematic study of the oxidation of 3-hydroxy-2-substituted isoindolin-1-ones (hy-droxylactams) and their conversion to the corresponding phthalimides was undertaken using three oxidants. Of special interest was the introduction of nickel peroxide (NiO2 ) as an oxidation system for hydroxylactams and comparison of its performance with the commonly used pyridinium chlorochromate (PCC) and iodoxybenzoic acid (IBX) reagents. Using a range of hydroxylactams, optimal conversions of these substrates to the corresponding imides was achieved with 50 equivalents of freshly prepared NiO2 in refluxing toluene over 5–32 h reaction times. By comparison, oxidations of the same substrates using PCC/silica gel (three equivalents) and IBX (three equivalents) required oxidation times of 1–3 h for full conversion but required lengthier purification. While nominal amounts (~25 mg) of substrate hydroxylactams were used to ascertain conversion, scale-up procedures using all three methods gave good to excellent isolated yields of imides.
Tunable System for Electrochemical Reduction of Ketones and Phthalimides
Chen, Gong,Qiao, Tianjiao,Wang, Yaxin,Zhang, Jian,Zhao, Jianyou
supporting information, p. 3297 - 3302 (2021/10/14)
Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N3/HN3 cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.
Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones
Bansode, Ajay H.,Suryavanshi, Gurunath
supporting information, p. 1390 - 1400 (2021/01/26)
A visible light-rose bengal-TBHP mediated, controlled oxidation of N-substituted 1,2,3,4-tetrahydroisoquinolines is developed for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and isoquinolin-1(2H)-ones. The present method feature's a broad substrate scope, good functional group tolerances, and the products were prepared in good to excellent yields. The developed methodology further demonstrated in the synthesis of isoindolo[2,1-b] isoquinolin-5(7H)-one (topoisomerase-I inhibitor). (Figure presented.).
