114858-39-8Relevant articles and documents
Cobalt oxide-carbon nanocatalysts with highly enhanced catalytic performance for the green synthesis of nitrogen heterocycles through the Friedl?nder condensation
Godino-Ojer, Marina,López-Peinado, Antonio J.,Maldonado-Hódar, Francisco J.,Bailón-García, Esther,Pérez-Mayoral, Elena
, p. 5637 - 5648 (2019)
A novel series of eco-sustainable catalysts developed by supporting CoO nanoparticles on different carbon supports, highly efficient in the synthesis of quinolines and naphthyridines, through the Friedl?nder condensation, are reported for the first time. Textural properties, dispersion and location of the Co-phase are influenced by the nature of the carbon support, Co-precursor salt and metal loading, having a significant impact on the catalytic performance. Thus, the presence of the mesopores and macropores in carbon aerogels together with the homogeneous distribution of the active phase favours the formation of product 3a as a function of the metal loading. However, an increase in the metal content when using CNTs indicates the formation of CoO aggregates and an optimal concentration of 3 wt% CoO was observed, providing the highest conversion values. The carbon-based catalysts herein reported can be considered to be a sustainable alternative having advantages such as easy preparation, superior stability and notably enhanced catalytic performance, operating at lower temperature and under solvent-free conditions.
Eco-friendly catalytic systems based on carbon-supported magnesium oxide materials for the friedl?nder condensation
Godino-Ojer, Marina,Lpez-Peinado, Antonio J.,Martn-Aranda, Rosa M.,Przepirski, Jacek,Prez-Mayoral, Elena,Soriano, Elena
, p. 3440 - 3447 (2014)
Carbon-supported MgO materials are excellent and sustainable catalysts for the synthesis of N-containing heterocyclic compounds by the Friedl?nder condensation under mild, solvent-free conditions. The results reported herein indicate that MgO is the most active catalytic species that accelerates the reaction compared with the catalytic behavior observed for the carbon material Norit RX3. On the basis of DFT calculations, a reaction mechanism that involves dual activation of the reacting structures by the catalyst is proposed. Oxide, outside: MgO supported on carbon is able to catalyze the synthesis of interesting N-containing heterocyclic compounds efficiently under mild conditions. MgO on the carbon surface is responsible for the catalytic behavior. These carbon materials are environmentally friendly catalysts for the Friedl?nder reaction.
An unexpected one-pot synthesis of multi-substituted quinolines via a cascade reaction of Michael/Staudinger/aza-Wittig/aromatization of ortho-azido-β-nitro-styrenes with various carbonyl compounds
Yu, Zhi-Hua,Zheng, Hu-Fei,Yuan, Wei,Tang, Zi-Long,Zhang, Ai-Dong,Shi, De-Qing
, p. 8137 - 8141 (2013)
Multi-substituted quinolines 3 were unexpectedly prepared from a cascade reaction of ortho-azido-β-nitro-styrenes with various carbonyl compounds. This method takes advantages of mild condition, simple work-up, high yield as well as wide substrate scope, which makes this method powerful for one-pot synthesis of multi-substituted quinolines.
Asymmetric synthesis of isoquinolinonaphthyridines catalyzed by a chiral Br?nsted acid
Li, Jianjun,Fu, Yiwei,Qin, Cong,Yu, Yang,Li, Hao,Wang, Wei
, p. 6474 - 6477 (2017)
A catalytic asymmetric method for the synthesis of chiral isoquinolinonaphthyridines has been developed. A chiral disulfonimide catalyzes a redox cyclization reaction between 2-methyl-3-aldehydeazaarenes and 1,2,3,4-tetrahydroisoquinolines to deliver a range of isoquinolinonaphthyridines with good to high yields (up to 91%) and up to 92:8 er.
Developing strategies for the preparation of Co-carbon catalysts involved in the free solvent selective synthesis of aza-heterocycles
Godino-Ojer,Martín-Aranda,Maldonado-Hódar,Pérez-Cadenas,Pérez-Mayoral
, p. 223 - 231 (2018)
We report herein different series of new zero valent Cobalt nanocarbons, as doped and supported aerogels, able to efficiently catalyze the reaction of 2-amino-5-chlorobenzaldehyde and β-ketoesters, via Friedl?nder reaction. The reaction works under solvent-free and mild conditions affording yields over 80% in only 30 min of reaction time. The catalysts could be reused almost during two consecutive cycles without almost any activity loss. A comparative study between supported and doped-carbon aerogels, as catalysts highly efficient in the reaction, has allowed to stablish the relationship between the catalyst structure and the catalytic performance. At this regard, different parameters such as carbonization temperature and surface chemistry on the aerogels under study have been also explored. As a result, although the carbon matrix is involved in the reaction, the Co(0) nanoparticles on the carbon surface are the predominant active catalytic species. Oxygen functionalities on the oxidized samples in the surroundings of Co(0) nanoparticles probably prevent the access of the reagents, notably decreasing their catalytic performance.
Acetic Acid Promoted Redox Annulations with Dual C-H Functionalization
Zhu, Zhengbo,Seidel, Daniel
supporting information, p. 2841 - 2844 (2017/06/07)
Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with 2-alkylquinoline-3-carbaldehydes as well as the corresponding 4-alkyl isomers and pyridine analogues. These processes involve dual C-H bond functionalization. Acetic acid
Visible-light-promoted iminyl-radical formation from Acyl oximes: A unified approach to pyridines, quinolines, and phenanthridines
Jiang, Heng,An, Xiaode,Tong, Kun,Zheng, Tianyi,Zhang, Yan,Yu, Shouyun
, p. 4055 - 4059 (2015/03/30)
A unified strategy involving visible-light-induced iminyl-radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac-[Ir(ppy)3] as a photoredox catalyst, the acyl oximes were converted by 1 e- reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N-containing arenes. These reactions proceeded with a broad range of substrates at room temperature in high yield. This strategy of visible-light-induced iminyl-radical formation was successfully applied to a five-step concise synthesis of benzo[c]phenanthridine alkaloids.
Lithium triflate (LiOTf): A highly efficient and reusable catalytic system for the synthesis of diversified quinolines under neat conditions
Atar, Amol B.,Dindulkar, Someshwer D.,Jeong, Yeon Tae
, p. 695 - 701 (2013/07/26)
A series of diverse polyfunctionalized quinolines were easily prepared in excellent yields via a Friedlander reaction of o-aminoaryl ketone or o-aminoaryl aldehyde with α-methylene ketones using lithium triflate as an expeditious catalyst under solvent free conditions. The protocol provides a practical and straightforward approach toward highly functionalized quinoline derivatives in excellent yields. The catalyst is easily recoverable and less sensitive to moisture, which makes this protocol more advantageous.
Hypoglycemic imidazoline compounds
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Page/Page column 92, (2010/02/05)
This invention relates to certain novel imidazoline compounds and analogues thereof, to their use for the treatment of diabetes, diabetic complications, metabolic disorders, or related diseases where impaired glucose disposal is present, to pharmaceutical compositions comprising them, and to processes for their preparation.
Hypoglycemic imidazoline compounds
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Page 110, (2010/11/29)
This invention relates to certain novel imidazoline compounds and analogues thereof, to their use for the treatment of diabetes, diabetic complications, metabolic disorders, or related diseases where impaired glucose disposal is present, to pharmaceutical compositions comprising them, and to processes for their preparation. The compounds have the following formula: whereinX is -O-, -S-, or -NR5-;R5 is hydrogen, C1-8 alkyl, or an amino protecting group;R1, R1', R2, and R3 are independently hydrogen or C1-8 alkyl;R1 and R2 optionally together form a bond and R1' and R3 are independently hydrogen or C1-8 alkyl;R1 and R2 optionally combine together with the carbon atoms to which they are attached form a C3-7 carbocyclic ring and R1' and R3 are independently hydrogen or C1-8 alkyl;R1 and R1' together with the carbon atom to which they are attached optionally combine to form a C3-7 spirocarbocyclic ring and R2 and R3 are independently hydrogen or C1-8 alkyl;R2 and R3 together with the carbon atom to which they are attached optionally combine to form a C3.7 spirocarbocyclic and R1 and R1' are independently hydrogen or C1-8 alkyl;n is 0, 1, or 2;m is 1 or2; 2;m' is 0, 1, or 2;q' is 0,1,2,3,4, or 5;R4 isY is -O-, -S-, or -NR8-;Y' is -O- or -S-;R6 and R7 are independently hydrogen, C1-8 alkyl, C3-7 cycloalkyl, C1-8 alkoxy, C1-8 alkylthio, halo C1-8 alkylthio, C1-8 alkylsulfinyl, C1-8 alkylsulfonyl. C3-7 cycloalkoxy, aryl-C1-8 alkoxy, halo, halo-C1-8 alkyl, halo-C1-8 alkoxy, nitro, -NR10R11, -CONR10R11, aryl C1-8 alkyl, optionally substituted heterocyclyl, optionally substituted phenyl, optionally substituted naphthyl, optionally halo substituted acylamino, cyano, hydroxy, COR12, halo C1-8 alkylsulfinyl, or halo C1-8 alkylsulfonyl, or alkoxyalkyl of the formulaCH3(CH2)p-O-(CH2)q-O-; wherep is 0, 1, 2, 3, or 4; andq is 1, 2, 3, 4, or 5;R12 is C1-8 alkyl or optionally substituted phenyl;R8 is hydrogen, C1-8 alkyl, halo-C1-8 alkyl, optionally substituted phenyl, optionally substituted heterocyclyl, COO C1-8 alkyl, optionally substituted COaryl, COC1-8 alkyl, SO2C1-8 alkyl, optionally substituted SO2 aryl, optionally substituted phenyl-C1-8 alkyl, CH3(CH2)p-O-(CH2)q-O-;R9 is hydrogen, halo, C1-8 alkyl, halo C1-8 alkyl, C1-8 alkylthio, halo C1-8 alkylthio, C3-7 cycloalkylthio, optionally substituted arylthio or heteroarylthio, C1-8 alkoxy, C3-8 cycloalkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, or optionally substituted aryl or heteroaryl, C3-7 cycloalkyl, halo C3-7 cycloalkyl, C3-7 cycloalkenyl, cyano, COOR10,CONR10R11 or NR10R11,C2-6 alkenyl, optionally substituted heterocyclyl, optionally substituted aryl C1-8 alkyl, optionally substituted heteroaryl C1-8 alkyl in which the alkyl group can be substituted by hydroxy, or C1-8 alkyl substituted by hydroxy,R10 and R11 are independently hydrogen, C1-8 alkyl, optionally substituted aryl C1-8 alkyl, optionally substituted phenyl, or R10 and R11 together with the nitrogen atom to which they are attached may combine to form a ring with up to six carbon atoms which optionally may be substituted with up to two C1-8 alkyl groups or one carbon atom may be replaced by oxygen or sulfur;R14 and R16 are independently hydrogen, halo, C1-8 alkyl, C3-7 cycloalkyl, C3-7 cycloalkoxy, C3-7 cycloalkylC1-8 alkoxy, halo-C1-8 alkyl, halo-C1-8 alkoxy, C1-8 alkoxy, carbo(C1-8)alkoxy, optionally substituted aryl, or optionally substituted heteroaryl;R15 and R17 are independently hydrogen, halo, C1-8 alkoxy, C3-7-cycloalkyl, C3-7 cycloalkylC1-8 alkoxy, C1-8 alkyl, C3-7 cycloalkoxy, hydroxy, halo C1-8 alkoxy, carbo(C1-8)alkoxy, optionally substituted phenyl, optionally substituted phenyl-C1-8 alkyl, optionally substituted phenyloxy, optionally substituted phenyl-C1-8 alkoxy, (tetrahydropyran-2-yl)methoxy, C1-8 alkyl-S(O)m-, optionally substituted aryl-C1-8 alkyl-S(O)m·-, CH3(CH2)p-Z1-(CH2)q-Z2-, or Z3-(CH2)q'-Z2-;Z1 and Z2 are independently abond, O, S, SO, SO2, sulphoximino, or NR10; andZ3 is hydroxy, protected hydroxy, NR10 R11, protected amino, SH or protected SH; ???provided that when R1, R1', R2 and R3 are all hydrogen; n is 0; R4 is naphthyl; and R14 R15 and R16, or R15, R16 and R17 are all hydrogen, then R17 or R14, respectively, is other than halo, methoxy, or C1-6 alkyl. ???or a pharmaceutically acceptable salt or ester thereof.
