91192-43-7Relevant academic research and scientific papers
Rapid eco-friendly synthesis and structure of 3-hydroxy-3-nitromethyl-1,3- dihydro-indol-2-one
Chen, Gang,Tang, Ying,Zhang, Qun-Zheng,Wu, Ya,Mu, Shun-Zhen
, p. 369 - 372 (2010)
3-Hydroxy-3-nitromethyl-1,3-dihydro-indol-2-one was synthesized from isatin by Henry reaction using an eco-friendly method and characterized by NMR and MS. The crystal structure was determined from single-crystal X-ray diffraction data. It crystallizes in the orthorhombic space group, Pbca, with unit cell dimensions a = 10.515 (2) A, b = 7.3736 (14) A, and c = 23.261 (4) A. The two rings are coplanar and the angle between hydroxyl group and nitromethyl group is 109.07(9)°. In the crystal structure, intermolecular N-H...;O and O-H...;O hydrogen bonds are responsible for the formation of a 3-dimensional network. No intramolecular hydrogen bond exists.
3-Hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one as a versatile intermediate for retro-Henry and Friedel-Crafts alkylation reactions in aqueous medium
Nagaraju, Sakkani,Sathish, Kota,Paplal, Banoth,Satyanarayana, Neeli,Kashinath, Dhurke
, p. 14045 - 14050 (2019/09/18)
The first example of a retro-Henry type reaction is reported using 3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-ones which are prepared via catalyst-free Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin. These compounds were used
Silver comes into play: Henry reaction and domino cycloisomerisation sequence catalysed by [Ag(i)(Pc-L)] complexes
Tseberlidis, Giorgio,Dell'Acqua, Monica,Valcarenghi, Daniele,Gallo, Emma,Rossi, Elisabetta,Abbiati, Giorgio,Caselli, Alessandro
, p. 97404 - 97419 (2016/10/25)
We report herein the synthesis of new pyridine-containing macrocyclic ligands (Pc-L) bearing a non-innocent pendant arm, by exploiting both chiral and functional properties of natural amino acids. The obtained macrocyclic ligands were employed to synthesize well-defined cationic silver(i) complexes that were shown to be competent catalysts for the Henry (nitroaldol) reaction. Good to excellent yields and full selectivity in the β-nitroalcohol product were obtained starting from electron-poor aromatic aldehydes or other activated aldehydes such as furfural under mild reaction conditions. The straightforward synthesis of the macrocyclic ligands starting from cheap commercially available starting materials allowed the introduction of a suitable basic functionality into the ligand pendant arm, thus providing a bifunctional catalyst. Based on our previous experience in the [Ag(i)(Pc-L)] catalysed domino addition/cycloisomerisation reaction of o-alkynylbenzaldehydes and nucleophiles, the synthesis of isochromenes coupling the Henry reaction and the cycloisomerisation in a single step was subsequently explored. Although with low selectivity, [Ag(i)(Pc-L)] cationic complexes were able to promote such a cascade reaction and a possible mechanism based on experimental evidence has been proposed.
Vasicine from Adhatoda vasica as an organocatalyst for metal-free Henry reaction and reductive heterocyclization of o-nitroacylbenzenes
Sharma, Sushila,Kumar, Manoranjan,Bhatt, Vinod,Nayal, Onkar S.,Thakur, Maheshwar S.,Kumar, Neeraj,Singh, Bikram,Sharma, Upendra
supporting information, p. 5003 - 5008 (2016/10/25)
Vasicine, a quinazoline alkaloid, from the leaves of Adhatoda vasica, has been utilized as an efficient catalyst for metal and base free Henry reaction of various aldehydes with nitro alkanes. The method can be used in the synthesis of various β-nitro alcohols under mild reaction conditions without use of hazardous organic solvents and expensive catalysts. Vasicine is also applied successfully for one pot synthesis of 2,1-benzisoxazoles from o-nitroacylbenzenes in good yields under mild conditions.
On water catalysis: An expeditious approach for the synthesis of quaternary centered 3-hydroxy-3-(nitromethyl)indolin-2-one derivatives
SaiPrathima, Parvathaneni,Srinivas, Keesara,Mohan Rao, Mandapati
supporting information, p. 2339 - 2343 (2015/04/22)
A novel, efficient, eco-friendly on water method has been developed for the Henry reaction of isatins with nitromethane to afford 3-hydroxy-3-nitromethylindolin-2-ones. An enhancement in reaction rate was observed on water under mild and catalyst-free conditions. This reaction tolerated a wide range of substrates with good to excellent product yields and is even applicable at large scales. Moreover, this method is environmentally friendly as it reduces the waste generated by the use of toxic solvents.
Copper-catalyzed enantioselective Friedel-Crafts alkylation of pyrrole with isatins
Li, Chong,Guo, Fengfeng,Xu, Kun,Zhang, Sheng,Hu, Yanbin,Zha, Zhenggen,Wang, Zhiyong
supporting information, p. 3192 - 3195 (2014/07/08)
The highly enantioselective Friedel-Crafts alkylation of pyrrole with isatins catalyzed by the tridentate Schiff base/Cu catalyst was developed. Hexafluoroisopropanol (HFIP) was used as a crucial additive to improve the enantioselectivity. In the case of N-unprotected isatins, an innovative substrate slow-releasing strategy was applied by virtue of a Henry/retro-Henry reaction.
3-SUBSTITUTED-3-HYDROXY OXINDOLE DERIVATIVES AND PROCESS FOR PREPARATION THEREOF
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Paragraph 0082-0083, (2014/02/15)
The present invention relates to expedient method for synthesis of 3-substituted-3-hydroxy-oxindole derivatives, which are useful as synthetic precursors to valuable pharmaceutical compounds. These are synthesized by reacting nitromethane with the corresp
Asymmetric nitroaldol reactions of nitroalkanes with isatins catalyzed by bifunctional cinchona alkaloid derivatives
Li, Mei-Qiu,Zhang, Jin-Xin,Huang, Xiao-Fei,Wu, Bin,Liu, Zhao-Min,Chen, Jian,Li, Xiang-Dong,Wang, Xing-Wang
scheme or table, p. 5237 - 5241 (2011/11/13)
The enantioselective nitroaldol reactions of isatins with nitroalkanes were smoothly carried out by organocatalysis. A C6′-OH cinchona alkaloid derivative bearing a C9-OBn group exhibited outstanding catalytic efficiency as an acid-base bifunctional catal
An efficient and environmentally friendly DABCO catalyzed Henry reaction of isatins
Meshram,Ramesh, Palakuri,Kumar, A. Sanjeeva,Swetha
experimental part, p. 5862 - 5864 (2011/12/03)
An efficient and general method has been described for the synthesis of 3-hydroxy-3-(nitromethyl)indolin- 2-one by the reaction of isatins with nitromethane/nitroethane in the presence of DABCO. The reaction is catalytic, very rapid, yields are very high
Catalytic enantioselective henry reactions of isatins: Application in the concise synthesis of (S)-(-)-spirobrassinin
Liu, Lu,Zhang, Shilei,Xue, Fei,Lou, Guangshun,Zhang, Haoyi,Ma, Shichao,Duan, Wenhu,Wang, Wei
scheme or table, p. 7791 - 7795 (2011/08/06)
When isatin a cat! A highly efficient, cupreine-catalyzed, enantioselective Henry reaction of readily available isatins and nitroalkanes has been developed (see scheme). The products are produced in excellent yields and good enantioselectivities under mild reaction conditions and without chromatography. The utility of the strategy has been demonstrated in the facile synthesis of (S)-(-)-spirobrassinin without the need for protecting groups. Copyright
