18167-15-2Relevant academic research and scientific papers
Reactions of imides with samarium(II) iodide
Brandukova,Vygodskii,Komarova,Strelkova
, p. 1176 - 1177 (1996)
The tendency of a series of imides and lactams to react with samarium(II) iodide was investigated. Under the action of SmI2 at ～20 °C, one of the carbonyl groups of N-phenylphthalimide was reduced to a CHOH or CH2 group depending on
Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
supporting information, p. 2298 - 2302 (2021/04/05)
An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.
Oxidative Desymmetrization of Isoindolines Realized by tert -Butyl Nitrite (TBN) Initiated Radical sp 3C-H Activation Relay (CHAR)
Sun, Zheng,Shao, Yu,Zhang, Shuwei,Zhang, Yuxian,Yuan, Yu,Jia, Xiaodong
, p. 1663 - 1671 (2021/02/01)
An oxidative desymmetrization of isoindolines was realized by TBN initiated radical sp 3C-H activation relay (CHAR), providing a series of ω-hydroxylactams in high yields. This reaction exhibits broad substrate scope and functional group tolerance, and even N -alkyl iso-indolines can be well tolerated. The mechanistic study shows that the C-H bond oxidation, dioxygen trapping and intramolecular 1,5-H shift might be the key steps to achieve the oxidative desymmetrization.
Preparation method of hydroxyl lactam
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Paragraph 0035; 0036; 0037; 0038, (2020/02/19)
The invention discloses a preparation method of hydroxyl lactam. The hydroxyl lactam is prepared from cyclic imide shown in a formula (II) through a homogeneous catalytic hydrogenation reaction, wherein R1, R2 and R3 are respectively and independently H,
Br?nsted acid mediated intramolecular cyclopropane ring expansion/[4 + 2]-cycloaddition
Li, Jian,Zhu, Shangrong,Xu, Qiuneng,Liu, Li,Yan, Shenghu
, p. 10004 - 10008 (2019/12/23)
A cascade reaction of 3-hydroxy-2-phenylisoindolin-1-one and cyclopropyl ketone has been developed via a Br?nsted acid-promoted ring-opening/intramolecular cross-cycloaddition/[4 + 2]-cycloaddition process. The developed methodology provides straightforward access to pentacyclic isoindolin-1-one derivatives under simple reaction conditions.
PdII/AgI-Catalyzed Room-Temperature Reaction of γ-Hydroxy Lactams: Mechanism, Scope, and Antistaphylococcal Activity
Dutta, Manali,Mandal, Santi M.,Pegu, Rupa,Pratihar, Sanjay
, p. 2193 - 2198 (2017/03/01)
The present work reports a PdII/AgI-promoted amidoalkylation reaction involving various γ-hydroxy lactams and C/O/S nucleophiles at room temperature. The dual mode of activation of both the electrophile and nucleophile by in situ generated catalytically active cationic PdII species facilitates the reaction at room temperature. Among the synthesized isoindoline derivatives, three compounds are found to be active against vancomycin and methicillin-resistant S. aureus strain with appreciable MIC values.
Facile synthesis of 3-substituted isoindolinones Dedicated to the memory of Professor Sharon Roscoe, a colleague and mentor instrumental in shaping the careers of many chemists
Al-Jaroudi, Zainab,Mohapatra, Prabhu P.,Jha, Amitabh
supporting information, p. 772 - 777 (2016/02/05)
The reactions of N-aryl-3-hydroxyisoindolinones and alkyl aryl ketones under Lewis acid-catalyzed anhydrous conditions afforded the corresponding substituted isoindolinones in good to excellent yields.
The behavior of 2-substituted-3-hydroxyisoindolinones in the reaction with sec-butyllithium
Jozwiak,Ciechanska
, p. 357 - 362 (2014/04/17)
This paper presents a dualistic behavior of 2-substituted-3- hydroxyisoindolones in reactions with sec-butyllithium (sec-BuLi). 2-tert-Butyl-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (1a) treated with sec-BuLi undergoes metalation at position 7. On the other hand, the reaction between 3-hydroxy-2-phenyl-2,3-dihydroxyisoindol-1-one (1j) and sec-BuLi results in 3-sec-butyl-2-phenyl-2,3-dihydroisiondol-1-one (3j).
Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
Jha, Amitabh,Chou, Ting-Yi,ALJaroudi, Zainab,Ellis, Bobby D.,Cameron, T. Stanley
supporting information, p. 848 - 857 (2014/05/06)
The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)- ones via [4 + 2] imino-DielsAlder cyclization from N-aryl-3- hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3- hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl) vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.
A Cu-catalysed synthesis of substituted 3-methyleneisoindolin-1-one
Gogoi, Anupal,Guin, Srimanta,Rout, Saroj K.,Majji, Ganesh,Patel, Bhisma K.
, p. 59902 - 59907 (2015/02/19)
A Cu(I)-catalysed synthesis of substituted 3-methyleneisoindolin-1-ones using alkynyl acids as an alkyne source has been developed. The reaction involves the decarboxylative cross-coupling of 2-halobenzamides with aryl alkynyl acids, followed by 5-exo-dig
