13720-91-7Relevant academic research and scientific papers
Cs2CO3-Promoted C?O Coupling Protocol Enables Solventless (Hetero)aryl Ether Synthesis under Air Atmosphere
Jiang, Bowen,Chen, Cheng,Fan, Guang-Gao,Sang, Wei,Cheng, Hua,Zhang, Rui,Yuan, Ye,Li, Qi-Zhong,Verpoort, Francis
supporting information, (2022/02/05)
In this work, a Cs2CO3-promoted synthetic approach was identified for (hetero)aryl ether synthesis via the C?O coupling of various (hetero)aryl chlorides and alcohols/phenol. To our delight, the reactions could be carried out under transition-metal-free and solvent-free conditions. Moreover, analytical-grade reagents and air atmosphere were readily tolerated. To showcase the practical usefulness of the present protocol, the assembly of a bioactive molecule was facilely realized and the gram-scale production of selected ether products was also efficiently accomplished. In addition, density functional theory (DFT) studies, along with a few mechanistic experiments, were conducted to elucidate a proposed reaction pathway and rationalize the pivotal role of Cs2CO3 in promoting this process. Hopefully, this work could provide useful information for researchers who are engaging in C?O cross-coupling reactions.
Synthesis of N-heterocyclic ligands for use in affinity and mixed mode chromatography
Mountford, Simon J.,Campi, Eva M.,Robinson, Andrea J.,Hearn, Milton T.W.
experimental part, p. 471 - 485 (2011/03/18)
A set of heterocyclic ligands have been synthesised for use in the preparation of mixed mode affinity chromatographic adsorbents for application in the purification of proteins, including antibodies. The ligand structures were designed to consist of a pyridinyl or related aza-heterocyclic nucleus bearing a pendant arm containing either an alkylamine, alkylthiol or hydroxyalkyl nucleophilic group to allow their facile immobilisation onto an activated support matrix. Ligand diversity was achieved by altering the length of the alkyl chain between the heterocyclic nucleus and nucleophilic group, varying the position of alkyl chain attachment to the heterocycle, and incorporating extra substituents into the pyridinyl or related aza-heterocyclic ring. This diversity in ligand structure was intended to enable key structural features of the ligand, required for efficient protein binding, to be determined. In contrast to the previously used multi-step procedures for the preparation of analogous substituted pyridine or aza-heterocyclic compounds, the synthesis routes for the ligands described here have generally utilized very mild, one-step reactions with readily available heterocyclic precursors. Copyright
A new synthesis of functionalized imidazol-2-ones
Wendeborn,Winkler,Foisy
, p. 6387 - 6391 (2007/10/03)
The novel preparation of imidazol-2-ones in four steps from quinolines via an oxidative ring rearrangement is reported. (C) 2000 Elsevier Science Ltd.
SYNTHESIS OF 4-ALKOXYQUINOLINES FROM QUINOLINE REISSERT COMPOUNDS
Sugiura, Michiharu,Sakurai, Yoshie,Hamada, Yoshiki
, p. 561 - 568 (2007/10/02)
The quinoline Reissert compound (5a) was converted to 1-benzoyl-3-bromo-2-cyano-1,2,3,4-tetrahydro-4-methoxyquinoline (6a) by successive treatment in methanol with bromine and aq. sodium carbonate.Hydrolysis of 6a with hydrochloric acid gave 3-bromoquinoline (4; R=H), but that with aq. sodium hydroxide afforded 4-methoxyquinoline (7a).Reissert compounds derived from some quinoline derivatives (5) gave the corresponding 4-methoxyquinolines (7) through tetrahydroquinolines (6) in a similar way.
