70867-38-8Relevant academic research and scientific papers
Design, synthesis and SAR of antitubercular benzylpiperazine ureas
Satish, Sohal,Chitral, Rohan,Kori, Amitkumar,Sharma, Basantkumar,Puttur, Jayashree,Khan, Afreen A.,Desle, Deepali,Raikuvar, Kavita,Korkegian, Aaron,Martis, Elvis A. F.,Iyer, Krishna R.,Coutinho, Evans C.,Parish, Tanya,Nandan, Santosh
, (2021/01/04)
Abstract: N-furfuryl piperazine ureas disclosed by scientists at GSK Tres Cantos were chosen as antimycobacterial hits from a phenotypic whole-cell screen. Bioisosteric replacement of the furan ring in the GSK Tres Cantos molecules with a phenyl ring led to molecule (I) with an MIC of 1?μM against Mtb H37Rv, low cellular toxicity (HepG2 IC50 ~ 80?μM), good DMPK properties and specificity for Mtb. With the aim of delineating the SAR associated with (I), fifty-five analogs were synthesized and screened against Mtb. The SAR suggests that the piperazine ring, benzyl urea and piperonyl moieties are essential signatures of this series. Active compounds in this series are metabolically stable, have low cellular toxicity and are valuable leads for optimization. Molecular docking suggests these molecules occupy the Q0 site of QcrB like Q203. Graphic Abstract: Bioisosteric replacement of N-furfuryl piperazine-1-carboxamides yielded molecule (I) a novel lead with satisfactory PD, metabolism, and toxicity profiles.[Figure not available: see fulltext.]
Method for preparing amine compound by alkali-catalyzed decarboxylation (by machine translation)
-
, (2020/03/25)
The method is simple and convenient (reaction conditions ;), more stable,atom utilization rate, by-products are only carbon dioxide pollution, and the yield can reach. suitable for industrial production Curtis; and the method, Lossen is suitable for industrial production . The method disclosed by the invention is simple and convenient to operate under the action of a base as, rearrangement, rearrangement reaction of an alkyl, aryl or heterocyclic aromatic carboxylic acid or an ester and hydroxylamine compound, 90%. (by machine translation)
Enantioselective Synthesis of cis- A nd trans-Borocyclopropylmethanol: Simple Building Blocks to Access Heterocycle-Substituted Cyclopropylmethanols
Charette, André B.,Navuluri, Chandrasekhar,Siddiqui, Saher H.
, p. 3834 - 3846 (2019/10/11)
An enantioselective and non-oxidative methodology was developed to obtain enantioenriched cyclopropyl boronates using a diethanolamine-promoted selective decomplexation of dioxaborolane. The non-oxidative decomplexation of the dioxaborolane ligand from the cyclopropylmethoxide species formed in the dioxaborolane-mediated Simmons-Smith cyclopropanation reaction provided the enantio?-enriched CIDA-based (CIDA = N-cyclohexyliminodiacetic acid) boro?-cyclopropane in 92% yield and 95.6:4.4 er. A robustness screen has shown diethanolamine to be compatible with esters, carbamates and N-heterocycles, providing a tool to access enantioenriched cyclopropanes carrying not only base-sensitive but oxidizable functional groups as well. Diethanolamine was found to be compatible with the modified zinco-cyclopropanation reaction of allyl alcohol to remove residual dioxaborolane from the corresponding cis-N-heterocycle cyclopropylmethanol, thereby leading to improved yields.
Direct ortho -Selective C-H Functionalization of Carboxybenzyl-Protected Arylalkylamines via Ir(III)-Catalyzed C-H Activation
Li, Guobao,Hu, Jundie,Zeng, Runsheng,Shi, Da-Qing,Zhao, Yingsheng
supporting information, p. 2454 - 2458 (2018/04/26)
A convenient and practical approach to synthesize ortho-alkynylated arylalkylamines through ortho-selective C-H functionalization has been developed using Cbz-amide as the directing group and Ir(III) as the catalyst. Various substrates were well tolerated, affording the corresponding products in moderate to good yields. Moreover, preliminary mechanistic study revealed the role of the amide as the coordination center to cooperate with the Ir(III) complex during C-H activation. Development of this Cbz-amide-promoted CAr-H functionalization offers a practical approach with potential applications in organic synthesis.
Base-Mediated Intramolecular Decarboxylative Synthesis of Alkylamines from Alkanoyloxycarbamates
Li, Peihe,Ma, Nuannuan,Wang, Zheng,Dai, Qipu,Hu, Changwen
, p. 8233 - 8240 (2018/05/31)
A general and effective method for the synthesis of alkylamine via intramolecular decarboxylation of alkanoyloxycarbamates is described. The alkanoyloxycarbamates are readily prepared with alkyl carboxylic acids and hydroxylamine. The reaction shows a broad range of substrates (primary and secondary alkyl) with functional tolerance, and the corresponding products were obtained in good yields under mild conditions.
A base-mediated self-propagative Lossen rearrangement of hydroxamic acids for the efficient and facile synthesis of aromatic and aliphatic primary amines
Ohtsuka, Naoya,Okuno, Moriaki,Hoshino, Yujiro,Honda, Kiyoshi
, p. 9046 - 9054 (2016/10/05)
A variety of aromatic and aliphatic hydroxamic acids were converted to the corresponding primary amines via base-mediated rearrangement. This rearrangement could proceed with less than 1 equiv. of K2CO3 in polar solvents under thermal conditions with no external reagents. This rearrangement has several features including no external activating agents needed for promoting the rearrangement, less than one equivalent of a base is sufficient for the reaction, and a clean reaction in which only carbon dioxide is produced as a by-product. A self-propagating mechanism via an isocyanate intermediate is proposed and elementary reaction steps, namely, chain propagation reactions are supported by experiments.
N-Urethane protection of amines and amino acids in an ionic liquid
Di Gioia,Gagliardi,Leggio,Leotta,Romio,Liguori
, p. 63407 - 63420 (2015/08/11)
An efficient, solvent-free protocol for the N-fluorenylmethoxycarbonylation and N-benzyloxycarbonylation of amines is described. The reaction of aliphatic and aromatic amines with FmocOSu and Cbz-Osu in [Bmim][BF4] at room temperature afforded the corresponding N-urethane derivatives in excellent yields and do not require any further purification. The method has been extended to the N-Fmoc and N-Cbz protection of amino acids. Absence of bases, very short reaction times, high yields, selectivity and ease of product separation are some advantages of this protocol.
Photocatalytic decarboxylative reduction of carboxylic acids and its application in asymmetric synthesis
Cassani, Carlo,Bergonzini, Giulia,Wallentin, Carl-Johan
supporting information, p. 4228 - 4231 (2014/09/30)
The decarboxylative reduction of naturally abundant carboxylic acids such as α-amino acids and α-hydroxy acids has been achieved via visible-light photoredox catalysis. By using an organocatalytic photoredox system, this method offers a mild and rapid entry to a variety of high-value compounds including medicinally relevant scaffolds. Regioselective decarboxylation is achieved when differently substituted dicarboxylic acids are employed. The application of this method to the synthesis of enantioenriched 1-aryl-2,2,2-trifluoroethyl chiral amines starting from natural α-amino acids further testifies to the utility of the developed photocatalytic decarboxylative reduction protocol.
Microwave-assisted expeditious synthesis of 5-fluoroalkyl-3-(aryl/alkyl)- oxazolidin-2-ones
Yang, Bo,Shi, Luyan,Wu, Jingjing,Fang, Xiang,Yang, Xueyan,Wu, Fanhong
supporting information, p. 3331 - 3337 (2013/04/24)
An efficient and convenient protocol for synthesis of 5-fluoroalkyl-3- (aryl/alkyl)-oxazolidin-2-ones is described. The reaction of allyl (aryl/alkyl) carbamates with fluoroalkyl iodide initiated by sodium dithionite in aqueous acetonitrile resulted in adducts that undergoes a cyclization assisted by microwave irradiation to form 5-fluoroalkyl-3-(aryl/alkyl)-oxazolidin-2-ones with high yields. It was also found that the products can be more efficiently formed via an AIBN-initiated one-pot addition-cyclization sequence from benzyl allyl(aryl/alkyl) carbamates and fluoroalkyl iodide.
A facile protocol for N-Cbz protection of amines in PEG-600
Zhang, Chun Lin,Zhang, Dong Feng,Zhao, Hong Yi,Lin, Zi Yun,Huang, Hai Hong
experimental part, p. 789 - 792 (2012/08/08)
An efficient and eco-friendly protocol for the chemoselective N-benzyloxycarbonylation of amines was described. The reaction of amines with benzyl chloroformate (Cbz-Cl) in the presence of PEG-600 at room temperature afforded the corresponding N-Cbz derivatives in excellent yields. The method is applicable to the N-Cbz protection of aliphatic (acyclic and cyclic) and aromatic amines.
