78660-85-2Relevant articles and documents
"on Water" Catalytic Aldol Reaction between Isatins and Acetophenones: Interfacial Hydrogen Bonding and Enamine Mechanism
Han, Jinsong,Zhang, Jin-Lei,Zhang, Wei-Qiang,Gao, Ziwei,Xu, Li-Wen,Jian, Yajun
, p. 7642 - 7651 (2019/06/17)
"On water" catalytic aldol reaction catalyzed by polyetheramine (D230) has been developed for easy access to 3-substituted 3-hydroxyindolin-2-ones through the reaction between various substituted isatins and acetophenones/cyclic ketones in high yields under room temperature. Systematic mechanism investigation uncovers the secret for the on water catalytic aldol reaction: comparison of the heterogeneous and homogeneous reaction circumstances with yields of 95 and 20%, respectively, indicates the on-water reaction dominating; interfacial hydrogen bonding between isatin with H2O is tested based on the downfield shift of the C2 and C3's 13C NMR signals when water was added to the CDCl3 solution of isatin; Lewis base polyetheramine D230 catalyzes the aldol reaction via the enamine mechanism verified by in situ NMR and ESI-MS analysis.
Highly efficient regioselective synthesis of pyrroles via a tandem enamine formation-Michael addition-cyclization sequence under catalyst- and solvent-free conditions
Vivekanand, Thavaraj,Vinoth, Perumal,Agieshkumar,Sampath, Natarajan,Sudalai, Arumugam,Menéndez, J. Carlos,Sridharan, Vellaisamy
supporting information, p. 3415 - 3423 (2015/06/25)
A convenient catalyst-free, three-component procedure was developed for the synthesis of tetrasubstituted pyrroles under solvent-free conditions and in green solvents glycerol, PEG-200 and water. A sequential enamine-formation, Michael addition and intram
Synthesis and antimicrobial activity of some novel 2-thienyl substituted heterocycles
Youssef, Mohamed Salah K.,Abeed, Ahmed Abdou O.
, p. 25 - 31 (2014/04/03)
A series of 2-thienyl substituted derivatives of thiazoles, oxazoles and spiro(indole-azole) were synthesized. The structures of the synthesized compounds were confirmed by IR, NMR and mass spectral data.
Chalcone based azacarboline analogues as novel antitubulin agents: Design, synthesis, biological evaluation and molecular modelling studies
Sharma, Sahil,Kaur, Charanjit,Budhiraja, Abhishek,Nepali, Kunal,Gupta, Manish K.,Saxena,Bedi
, p. 648 - 660 (2014/09/17)
The present study involves the design of a series of 3-aryl-9-acetyl- pyridazino[3,4-b]indoles as constrained chalcone analogues. A retrosynthetic route was proposed for the synthesis of target compounds. All the synthesized compounds were evaluated for in-vitro cytotoxicity against THP-1, COLO-205, HCT-116 and A-549 human cancer cell lines. The results indicated that 2a, 3a, 5a and 6a possessed significant cytotoxic potential with an IC50 value ranging from 1.13 to 5.76 μM. Structure activity relationship revealed that the nature of both Ring A and Ring B influences the activity. Substitution of methoxy groups on the phenyl ring (Ring A) and unsubstituted phenyl ring (Ring B) were found to be the preferred structural features. The most potent compound 2a was further tested for tubulin inhibition. Compound 2a was found to significantly inhibit the tubulin polymerization (IC50 value - 2.41 μM against THP-1). Compound 2a also caused disruption of microtubule assembly as evidenced by Immunoflourescence technique. The significant cytotoxicity and tubulin inhibition by 2a was rationalized by molecular modelling studies. The most potent structure was docked at colchicine binding site (PDB ID-1SA0) and was found to be stabilized in the cavity via various hydrophobic and hydrogen bonding interactions.
Molecular sieve mediated decarboxylative Mannich and aldol reactions of β-ketoacids
Zhong, Fangrui,Jiang, Chunhui,Yao, Weijun,Xu, Li-Wen,Lu, Yixin
supporting information, p. 4333 - 4336 (2013/07/26)
A molecular sieve mediated decarboxylative Mannich reaction of β-ketoacids with sulfonyl imines is reported; this protocol leads to an efficient preparation of synthetically useful β-amino ketones. An analogous molecular sieve promoted decarboxylative aldol reaction between β-ketoacids and isatins is also described, which affords bioactive 3-substituted-3-hydroxy-oxindoles in excellent yields.
Hydrogen-bonding patterns in 3-alkyl-3-hydroxy-indolin-2-ones
Becerra, Diana,Insuasty, Braulio,Cobo, Justo,Glidewell, Christopher
scheme or table, p. o79-o86 (2010/06/20)
The mol-ecules of racemic 3-benzoyl-methyl-3-hydroxy-indolin-2-one, C 16H13NO3, (I), are linked by a combination of N-H...O and O-H...O hydrogen bonds into a chain of centrosymmetric edge-fused R 2 2(10) and R 4
Catalyst-free aldol condensation of ketones and isatins under mild reaction conditions in DMF with molecular sieves 4 A as additive
Chen, Wen-Bing,Liao, Yu-Hua,Du, Xi-Lin,Zhang, Xiao-Mei,Yuan, Wei-Cheng
experimental part, p. 1465 - 1476 (2010/05/18)
In the presence of molecular sieve (MS) 4 A in DMF, a catalyst-free aldol condensation of a variety of aromatic and aliphatic ketones with isatins under mild reaction conditions has been developed. This approach may provide access to a wide range of 3-sub
Synthesis of Annulated Carbazoles from Indol-2,3-dione
Beccalli, Egle M.,Marchesini, Alessandro,Pilati, Tullio
, p. 4741 - 4758 (2007/10/02)
Reaction of ethyl chloroformate with 3-aroylmethylindol-2(3H)-ones 5 affords the ethyl 3--2-(ethoxycarbonyloxy)indole-1-carboxylates 6 from which the corresponding annulated carbazoles 10 are obtained via 6?-electro
Potential anticonvulsants. V. The condensation of isatins with C-acetyl heterocyclic compounds
Popp
, p. 589 - 592 (2007/10/02)
A number of C-acetyl heterocyclic compounds were condensed with isatin and substituted isatins to give a series of 3-hydroxy-3-substituted oxindoles. The products from 2-acetylfuran and isatin, 2-acetylthiophene and isatin, and 2-acetylpyridine and 1-meth
