17416-52-3Relevant academic research and scientific papers
Copper-catalysed synthesis of 3-hydroxyisoindolin-1-ones from benzylcyanide 2-iodobenzamides
Kavala, Veerababurao,Wang, Chen-Yu,Wang, Cheng-Chuan,Patil, Prakash Bhimrao,Fang, ChiaChi,Kuo, Chun-Wei,Yao, Ching-Fa
, p. 988 - 998 (2020/02/15)
An efficient one-pot two-step sequential reaction for the synthesis of biologically active 3-hydroxyisoindolin-1-one derivatives from 2-iodobenzamide derivatives and various substituted benzyl cyanides in the presence of CuCl and cesium carbonate in DMSO is reported. Furthermore, 3-hydroxyisoindolinone derivatives possessing bromo substituents were obtained from 2-iodobenzamide and 2-bromobenzyl cyanide substrates in two steps. Benzyl cyanide has been successfully used for the first time as a benzoyl synthon for the synthesis of 3-hydroxyisoindolin-1-ones. Interestingly, the mechanism of formation of 3-hydroxyisoindolin-1-ones is a novel pathway that involves carbon degradation followed by ring contraction.
Eosin Y as a Redox Catalyst and Photosensitizer for Sequential Benzylic C?H Amination and Oxidation
Yan, Dong-Mei,Zhao, Quan-Qing,Rao, Li,Chen, Jia-Rong,Xiao, Wen-Jing
, p. 16895 - 16901 (2018/10/26)
A new synergistic multicatalytic activation mode of eosin Y has been discovered by exploiting the redox potential of its ground state and excited state. This catalytic strategy proves to be an enabling tool for visible-light-driven sequential benzylic C?H amination and oxidation of o-benzyl-N-methoxyl-benzamides when using Selectfluor as a hydrogen atom transfer (HAT) reagent and O2 as oxidant. Efficient synthesis of a range of diversely functionalized 3-hydroxyisoindolinones can thus be achieved with good yields and selectivity at mild reaction conditions. Preliminary mechanistic studies and DFT calculations suggest that eosin Y works as a redox catalyst and photosensitizer.
Base-promoted cascade C-C coupling/N-α-sp3C-H hydroxylation for the regiospecific synthesis of 3-hydroxyisoindolinones
Shen, Jinhai,You, Qihua,Fu, Qi,Kuai, Changsheng,Huang, Huabin,Zhao, Li,Zhuang, Zhixia
supporting information, p. 5170 - 5173 (2017/11/06)
A base-promoted cascade reaction for the regiospecific synthesis of substituted 3-hydroxyisoindolinones under transition-metal-free conditions is developed. The base-mediated C-C bond coupling and N-α-sp3C-H bond hydroxylation are involved in t
3-hydroxy isoindole-1-ketone derivative and preparation method thereof
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Paragraph 0051; 0052; 0053; 0054, (2017/11/04)
The invention discloses a preparation method of a 3-hydroxy isoindole-1-ketone derivative (formula 2). A compound as shown by formula (1) is used for carrying out substitution reaction in a solvent in the presence of alkali and air to obtain the 3-hydroxy
Hydrogenolysis of the C-O bond of hydroxylactams as a convenient method for the synthesis of substituted isoindolin-1-ones
Sagirova,Starodubtseva,Turova,Vinogradov
, p. 1032 - 1037 (2014/03/21)
A simple and efficient method for the synthesis of isoindolin-1-ones containing alkyl or aryl substituents at positions 2 and (or) 3 was suggested. The method is based on the earlier unknown Pd0-catalyzed hydrogenolysis of hydroxylactams.
Total spontaneous resolution by deracemization of isoindolinones
Yagishita, Fumitoshi,Ishikawa, Hiroki,Onuki, Tatsuo,Hachiya, Shoko,Mino, Takashi,Sakamoto, Masami
supporting information, p. 13023 - 13025 (2013/03/13)
Preferential crystallization is a powerful tool to obtain optically active materials from racemic mixtures without any chiral source, and has been utilized widely for optical resolution on large scales for example in industrial processes.[ 1] To resolve optically active materials by crystallization efficiently, dynamic preferential crystallization involving a racemization process, a so-called total spontaneous resolution, has been developed.[2] Many efforts have been invested in new variations of this method, and the racemization processes can be classified into three groups: 1) involving an intermediate enolate anion or enol at the a-position of a carbonyl group,[3] 2) involving atropisomerism of axially chiral materials,[4] and 3) involving an equilibrium reaction via an achiral intermediate.[5-7] We have now developed a new example of total spontaneous resolution of isoindolinones that involves a combination of an intramolecular equilibrium reaction via an achiral intermediate and preferential crystallization.
Small-molecule inhibitors of the MDM2-p53 protein-protein interaction based on an isoindolinone scaffold
Hardcastle, Ian R.,Ahmed, Shafiq U.,Atkins, Helen,Farnie, Gillian,Golding, Bernard T.,Griffin, Roger J.,Guyenne, Sabrina,Hutton, Claire,K?llblad, Per,Kemp, Stuart J.,Kitching, Martin S.,Newell, David R.,Norbedo, Stefano,Northen, Julian S.,Reid, Rebecca J.,Saravanan,Willems, Henri?tte M. G.,Lunec, John
, p. 6209 - 6221 (2007/10/03)
From a set of weakly potent lead compounds, using in silico screening and small library synthesis, a series of 2-alkyl-3-aryl-3-alkoxyisoindolinones has been identified as inhibitors of the MDM2-p53 interaction. Two of the most potent compounds, 2-benzyl-3-(4-chlorophenyl)-3-(3-hydroxypropoxy)-2,3- dihydroisoindol-1-one (76; IC50 = 15.9 ± 0.8 μM) and 3-(4-chlorophenyl)-3-(4-hydroxy-3,5-dimethoxybenzyloxy)-2-propyl-2, 3-dihydroisoindol-1-one (79; IC50 = 5.3 ± 0.9 μM), induced p53-dependent gene transcription, in a dose-dependent manner, in the MDM2 amplified, SJSA human sarcoma cell line.
Anionic ring-enlarging reaction of a hemiaminal system: Stereoselective approach to disubstituted tetrahydroisoquinolone
Tomooka, Katsuhiko,Tomoyasu, Takahiro,Hanji, Takayuki,Igawa, Kazunobu
, p. 2449 - 2453 (2008/02/10)
Treatment of N-substituted phthalimide-derived hemiaminal with alkyllithium led to tetrahydroisoquinolones with high diastereoselectivity. Mechanistic studies furnish persuasive evidence that the present ring-enlarging reaction proceeds via tautomerizatio
Isoindolinone-based inhibitors of the MDM2-p53 protein-protein interaction
Hardcastle, Ian R.,Ahmed, Shafiq U.,Atkins, Helen,Calvert, A. Hilary,Curtin, Nicola J.,Farnie, Gillian,Golding, Bernard T.,Griffin, Roger J.,Guyenne, Sabrina,Hutton, Claire,Kaellblad, Per,Kemp, Stuart J.,Kitching, Martin S.,Newell, David R.,Norbedo, Stefano,Northen, Julian S.,Reid, Rebecca J.,Saravanan,Willems, Henriette M.G.,Lunec, John
, p. 1515 - 1520 (2007/10/03)
A series of 2-N-alkyl-3-aryl-3-alkoxyisoindolinones has been synthesised and evaluated as inhibitors of the MDM2-p53 interaction. The most potent compound, 3-(4-chlorophenyl)-3-(4-hydroxy-3,5-dimethoxybenzyloxy)-2-propyl-2,3- dihydroisoindol-1-one (NU8231), exhibited an IC50 of 5.3 ± 0.9 μM in an ELISA assay, and induced p53-dependent gene transcription in a dose-dependent manner, in the SJSA human sarcoma cell line.
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.
