6273-59-2Relevant academic research and scientific papers
A novel copper framework with amino tridentate N-donor ligand as heterogeneous catalyst for ring opening of epoxides
Huang, Zi-Qing,Xu, Zou-Hong,Liu, Xiao-Hui,Zhao, Yue,Wang, Peng,Liu, Zhi-Qiang,Sun, Wei-Yin
, (2021/04/22)
A novel metal–organic framework (MOF) [Cu3L(2,6-NDC)2]·0.5DMF (MOF-Cu-1) was synthesized by solvothermal reaction of copper nitrate trihydrate with 2,6-naphthalenedicarboxylic acid (2,6-H2NDC) and amino tridentate N-donor
Selective Synthesis of Secondary Amines from Nitriles by a User-Friendly Cobalt Catalyst
Sharma, Dipesh M.,Punji, Benudhar
supporting information, p. 3930 - 3936 (2019/07/12)
Selective hydrogenation/reductive amination of nitriles to secondary amines catalyzed by an inexpensive and user-friendly cobalt complex, (Xantphos)CoCl2, is reported. The use of (Xantphos)CoCl2 and ammonia borane (NH3?BH3) combination affords the selective reduction of nitriles to symmetrical secondary amines, whereas the employment of (Xantphos)CoCl2 and dimethylamine borane (Me2NH?BH3) along with external amines produce unsymmetrical secondary amines and tertiary amines. The general applicability of this methodology is demonstrated by the synthesis of 43 symmetrical and unsymmetrical secondary and tertiary amines bearing diverse functionalities. (Figure presented.).
β-amino alcohols and their respective 2-phenyl-N-alkyl aziridines as potential DNA minor groove binders
Vaidergorn, Miguel M.,Carneiro, Zumira A.,Lopes, Carla D.,de Albuquerque, Sérgio,Reis, Felipe C.C.,Nikolaou, Sofia,Mello, Juliana F.R. e,Genesi, Giovani L.,Trossini, Gustavo H.G.,Ganesan,Emery, Flavio S.
, p. 657 - 664 (2018/08/23)
It is known that aziridines and nitrogen mustards exert their biological activities, especially in chemotherapy, via DNA alkylation. The studied scaffold, 2-phenyl-1-aziridine, provides a distinct conformation compared to commonly used aziridines, and the
Green Regio- and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent-Free Conditions
Acocella, Maria Rosaria,D'Urso, Luciana,Maggio, Mario,Guerra, Gaetano
, p. 1915 - 1920 (2016/07/06)
The ring-opening reactions of epoxides with amines were efficiently and regioselectively catalyzed by high-surface-area graphite and graphene oxide under metal-free and solvent-free conditions. For epoxides without aryl groups, catalytic activity was observed only for graphene oxide, and hence, the activity must have been due to its acidic groups. For styrene oxide, instead, graphite and graphene oxide exhibited rather similar catalytic activities, and hence, the activity was mainly due to activation of the electrophilic epoxide by π-stacking interactions with the graphitic π system. The described aminolysis procedure is green and cheap because the catalyst can be recovered and recycled without loss of efficiency. Moreover, these heterogeneous catalysts exert high stereoselective control in the presence of nonracemic epoxides and provide chiral β-amino alcohols with enantiomeric excess values up to 99 %.
Greener aminolysis of epoxides on BiCl3/SiO2
Mohsenzadeh, Farshid,Aghapoor, Kioumars,Darabi, Hossein Reza,Jalali, Mohammad Reza,Halvagar, Mohammad Reza
, p. 978 - 985 (2016/08/08)
The remarkable catalytic activity of BiCl3/SiO2 for the ring-opening of epoxides with aromatic and aliphatic amines under microwave and thermal heating was observed. This eco-friendly heterogeneous catalyst displayed high to excellent regioselectivity in the synthesis of β-amino alcohols under solvent-free conditions. High turnover frequency (TOF) values under microwave heating and excellent reusability of the catalyst may significantly contribute to applied chemistry.
Identification of novel 2-((1-(benzyl(2-hydroxy-2-phenylethyl)amino)-1-oxo- 3-phenylpropan-2-yl)carbamoyl)benzoic acid analogues as BMP-2 stimulators
Balaramnavar, Vishal M.,Khan, Imran A.,Siddiqui, Jawed Akhtar,Khan, Mohd Parvez,Chakravarti, Bandana,Sharan, Kunal,Swarnkar, Gaurav,Rastogi, Namrata,Siddiqui,Mishra, Durga Prasad,Chattopadhyay, Naibedya,Saxena, Anil K.
, p. 8248 - 8259 (2013/01/15)
The synthesis and SAR studies of 10 new chemical entities (NCEs) that have shown BMP-2 stimulation and osteoblast differentiation are reported. Among these, 2-((1-(benzyl(2-hydroxy-2-phenylethyl)amino)-1-oxo-3-phenylpropan-2-yl) carbamoyl)benzoic acid (11) was the most effective while its analogue 13 also showed good activity in inducing osteoblast BMP-2 production. Compound 11 induced osteoblast differentiation in vitro, and this effect was abrogated by a physiological BMP-2 inhibitor, noggin. It also exhibited dose dependent increase in nascent bone formation (2.16- and 3.12-fold more than the control at 1 and 5 mg/kg dose, respectively) at the fracture site in rats. At the maximum osteogenic concentration, compound 11 significantly inhibited osteoblastic proteosomal activity. This compound was safe, as it had no effect on BMP synthesis in cardiovascular tissue.
Synthesis and 2D QSAR of O-sulphonated β-aminols derivatives as novel antifungal and antibacterial agents
Saxena, Anil K.,Sharma, Sugandha,Pandey, Atindra K.,Shukla, Praveen K.
supporting information; experimental part, p. 6476 - 6481 (2011/11/29)
Synthesis of a series of b-aminol derivatives using regioselective opening reaction catalyzed by SiO2 (60-120 mesh) and O-sulphonation in THF-KOH system, comprising tert-butoxycarbonyl at secondary nitrogen and evaluate for various stains of bacteria and fungi. SAR study of synthesized compound using backward regression analysis.
Zinc tetrafluoroborate hydrate as a mild catalyst for epoxide ring opening with amines: Scope and limitations of metal tetrafluoroborates and applications in the synthesis of antihypertensive drugs (RS)/(R)/(S)-metoprolols
Pujala, Brahmam,Rana, Shivani,Chakraborti, Asit K.
experimental part, p. 8768 - 8780 (2011/12/04)
The scope and limitations of metal tetrafluoroborates have been studied for epoxide ring-opening reaction with amines, and Zn(BF4) 2?xH2O has been found to be a mild and efficient catalyst affording high yields under solvent-free conditions at rt with excellent chemo-, regio-, and stereoselectivities. The catalytic efficiency followed the order Zn(BF4)2?xH2O ? Cu(BF4)2?xH2O > Co(BF4) 2?6H2O ? Fe(BF4)2? 6H2O > LiBF4 for reactions with cyclohexene oxide and Zn(BF4)2?xH2O ? Co(BF4) 2?6H2O ? Fe(BF4)2? 6H2O > Cu(BF4)2?xH2O for stilbene oxide, but AgBF4 was ineffective. For reaction of styrene oxide with aniline, the metal tetrafluoroborates exhibited comparable regioselectivity (1:99-7:93) with preferential reaction at the benzylic carbon of the epoxide ring. A reversal of regioselectivity (91:1-69:31) in favor of the reaction at the terminal carbon of the epoxide ring was observed for reaction with morpholine. The regioselectivity was dependent on the electronic and steric factors of the epoxide and the pKa of the amine and independent of amine nucleophilicity. The role of the metal tetrafluoroborates is envisaged as "electrophile nucleophile dual activation" through cooperativity of coordination, charge-charge interaction, and hydrogen-bond formation that rationalizes the catalytic efficiency, substrate reactivity, and regioselectivity. The methodology was used for synthesis of cardiovascular drug metoprolol as racemic and enriched enantiomeric forms.
Heterogeneous Lewis acid catalysis with self-organized polymeric rare earth arylsulfonates under solvent-free conditions
Furuno, Hiroshi,Ishida, Shuichi,Suzuki, Shoko,Hayano, Tetsuji,Onitsuka, Satoaki,Inanaga, Junji
scheme or table, p. 1007 - 1018 (2010/10/03)
Polymeric rare earth arylsulfonates, easily prepared from rare earth triisopropoxides and biphenyl-4,4'-disulfonic acid (BPDSA) or 1,3,5-triphenylbenzene trisulfonic acid (TPTSA) in a self-organization manner, were found to work as an efficient heterogene
Regioselective ring-opening of epoxides with amines using Zn(ClO4)2-Al2O3 as a heterogeneous and recyclable catalyst
Maheswara, Muchchintala,Rao, Kummari Subba Venkata Krishna,Do, Jung Yun
, p. 1795 - 1800 (2008/09/18)
A simple and efficient method has been developed for the synthesis of β-amino alcohols by regioselective ring-opening of epoxides with amines in the presence of zinc perchlorate-neutral alumina as a heterogeneous recyclable catalyst at room temperature in high yields.
