97619-01-7Relevant academic research and scientific papers
Synthesis of new C-3 substituted kynurenic acid derivatives
Csámpai, Antal,Fül?p, Ferenc,Lorinczi, Bálint,Szatmári, István
, (2020/02/29)
The application of kynurenic acid (KYNA) as an electron-rich aromatic system in the modified Mannich reaction has been examined. The extension possibility of the reaction was tested by using amines occurring in a number of bioactive products, such as morpholine, piperidine, or N-methylpiperazine and aldehydes of markedly different reactivities, like formaldehyde and benzaldehyde. The influence of substituents attached to position 3 on the aminoalkylation was also investigated. Thus, reactions of 3-carbamoyl-substituted precursors with tertiary amine containing side-chains were also tested to afford new KYNA derivatives with two potential cationic centers. By means of NMR spectroscopic measurements, supported by DFT calculations, the dominant tautomer form of KYNA derivatives was also determined.
Hypervalent iodine(III)-promoted: N -incorporation into N -aryl vinylogous carbamates to quinoxaline diesters: Access to 1,4,5,8-tetraazaphenanthrene
Sagar,Vidaycharan, Shinde,Shinde, Anand H.,Sharada, Duddu S.
supporting information, p. 4018 - 4022 (2016/06/14)
A novel oxidative N-incorporation strategy for synthesis of quinoxaline diesters under metal-free conditions is described for the first time. The mild reaction conditions allow for this transformation via the formation of two C(sp2)-N bonds utilizing cheaply available NaN3 as the N-atom source. N-Aryl vinylogous carbamates in this study undergo azidation at enamino C(sp2)-H selectively. The robustness of this strategy is further demonstrated by the synthesis of a valuable 1,4,5,8-tetraazaphenanthrene derivative using a mild and convenient approach.
An eco-friendly sequential catalyst- and solvent-free four-component stereoselective synthesis of novel 1,4-pyranonaphthoquinones
Devi Bala, Balasubramanian,Michael Rajesh, Stephen,Perumal, Subbu
, p. 2484 - 2490 (2013/02/21)
A series of novel highly functionalized 1,4-pyranonaphthoquinones has been synthesized stereoselectively from one-pot sequential reactions of anilines, diethyl acetylenedicarboxylate, 2-hydroxynaphthalene-1,4-dione and benzaldehydes under microwave irradiation. This solvent- and catalyst-free transformation affording biologically relevant heterocycles presumably involves two Michael additions, aldol condensation and annulation reactions.
Practical synthesis and mechanistic study of polysubstituted tetrahydropyrimidines with use of domino multicomponent reactions
Zhu, Qiuhua,Jiang, Huanfeng,Li, Jinghao,Zhang, Min,Wang, Xiujun,Qi, Chaorong
experimental part, p. 4604 - 4613 (2009/10/02)
The practical synthesis of polysubstituted tetrahydropyrimidines 4 from but-2-ynedioates 1, amines 2, and formaldehyde 3 through a domino process of one-pot multicomponent reactions (MCRs) and the detailed mechanistic studies are described. The MCRs were
L-Proline-catalyzed synthesis of highly functionalized multisubstituted 1,4-dihydropyridines
Jiang, Huanfeng,Mai, Ronghuan,Cao, Hua,Zhu, Qiuhua,Liu, Xiaohang
supporting information; scheme or table, p. 4943 - 4953 (2010/02/16)
Highly functionalized multisubstituted 1,4-dihydropyridines 5 have been concisely synthesized in moderate to good yields vial-proline-catalyzed one-pot multicomponent reactions (MCRs) of alkynoates or alkynones 1, amines 2, β-dicarbonyl compounds 3 and aldehydes 4 under mild conditions. The MCR process involves hydroamination/Knoevenagel condensation/Michael-type addition/intramolecular cyclization processes and leads to the formation of 1,4-dihydropyridines 5. The molecular structure of 5ckaa was confirmed by single-crystal X-ray diffraction. This method is energy saving and environmentally friendly, providing easy access to diverse multisubstituted polyfunctional 1,4-dihydropyridines. The Royal Society of Chemistry 2009.
