38101-93-8Relevant academic research and scientific papers
Theoretical and experimental investigations of large stokes shift fluorophores based on a quinoline scaffold
Czaplinska, Barbara,Korzec, Mateusz,Malarz, Katarzyna,Mrozek-Wilczkiewicz, Anna,Musiol, Robert,Slodek, Aneta
, (2020)
A series of novel styrylquinolines with the benzylidene imine moiety were synthesized and spectroscopically characterized for their applicability in cellular staining. The spectroscopic study revealed absorption in the ultraviolet–visible region (360–380
Ru(II)–NNO pincer-type complexes catalysed E-olefination of alkyl-substituted quinolines/pyrazines utilizing primary alcohols
Tamilthendral, Veerappan,Balamurugan, Gunasekaran,Ramesh, Rengan,Malecki, Jan Grzegorz
, (2022/01/08)
An efficient and selective E-olefination of alkyl-substituted quinolines and pyrazines through acceptorless dehydrogenative coupling of alcohols catalysed by Ru(II)–N^N^O pincer-type complexes encompassing carbonyl and triphenylarsines as co-ligands is de
Nickel(II)-Catalyzed Selective (E)-Olefination of Methyl Heteroarenes Using Benzyl Alcohols via Acceptorless Dehydrogenative Coupling Reaction
Balamurugan, Gunasekaran,Ramesh, Rengan
, (2021/11/30)
An efficient catalytic protocol for the synthesis of selective (E)-olefins by the newly synthesized nickel complexes via greener acceptorless dehydrogenative coupling methodology is presented. Two nickel(II) N, S chelating complexes were structurally characterized with the aid of spectral and single crystal X-ray diffraction methods. Olefination of 2-methylheteroarenes with benzyl alcohols via acceptorless dehydrogenative coupling is achieved by inexpensive nickel(II) catalysts. The present olefination protocol is simple and furnishes the desired 2-alkenylheteroarenes in 35 h and yields in the range of 40–93 %. The dehydrogenative coupling reaction proceeds via the generation of an aldehyde intermediate and produces water and hydrogen as sole by-products. The wide substrate scope of this catalytic reaction covered the synthesis of drug intermediates.
NaCl as Catalyst and Water as Solvent: Highly E-Selective Olefination of Methyl Substituted N-Heteroarenes with Benzyl Amines and Alcohols
Hazra, Susanta,Tiwari, Vikas,Verma, Ashutosh,Dolui, Pritam,Elias, Anil J.
supporting information, p. 5496 - 5501 (2020/07/14)
Oxidative coupling of benzylamines and alcohols with methyl substituted N-heteroarenes such as quinolines and quinoxalines has been achieved using chloride, a sea abundant anion as the catalyst for practical synthesis of a wide range of E-disubstituted olefins in aqueous medium. Detailed mechanistic studies and control experiments were carried out to deduce the reaction mechanism which indicated that in situ formed ClO2- is the active form of the catalyst. We have successfully carried out a 1 g scale reaction using this methodology, and five pharmaceutically relevant conjugated olefins were also synthesized by this method in moderate to good yields.
Direct Alkenylation of 2-Methylquinolines with Aldehydes through Synergistic Catalysis of 1,3-Dimethylbarbituric Acid and HOAc
Liang, En,Wang, Junqi,Wu, Yinrong,Huang, Liangbin,Yao, Xingang,Tang, Xiaodong
supporting information, p. 3619 - 3623 (2019/07/10)
An efficient and practical direct alkenylation of 2-methylquinolines with aldehydes has been achieved through a novel synergistic organocatalysis. The HOAc- activated 2-methylquiolines undergo a Michael addition to 1,3-dimethylbarbituric acid-activated aldehydes, followed by a retro-Michael addition to release 1,3-dimethylbarbituric acid and the target products. The transformation produced various 2-alkenylquinolines with good to excellent yields and featured mild reaction conditions, atom- and step-economy, good functional group tolerance, and operational simplicity. (Figure presented.).
Iron-Catalyzed Coupling of Methyl N-Heteroarenes with Primary Alcohols: Direct Access to E-Selective Olefins
Das, Jagadish,Vellakkaran, Mari,Sk, Motahar,Banerjee, Debasis
supporting information, p. 7514 - 7518 (2019/10/02)
An efficient Fe-catalyzed system is reported for direct α-olefination of methyl-substituted N-heteroarenes with primary alcohols. The catalytic dehydrogenative coupling enables a series of functionalized E-olefinated N-heteroaromatics with excellent selectivity (>99%). Initial mechanistic studies including deuterium-labeling experiments provide evidence for the participation of the benzylic C-H/D bond of alcohols.
Synthesis of (E)-2-Alkenylazaarenes via Dehydrogenative Coupling of (Hetero)aryl-fused 2-Alkylcyclic Amines and Aldehydes with a Cobalt Nanocatalyst
Zhou, Changjian,Tan, Zhenda,Jiang, Huanfeng,Zhang, Min
, p. 2887 - 2892 (2018/05/03)
To date, the synthesis of (E)-2-alkenylazaarenes via the condensation of 2-methyl N-heteroarenes with aldehydes or their equivalents has been well demonstrated. However, the direct formation of such a class of useful compounds from extensively distributed 2-alkylcyclic amine motifs remains an unresolved goal. Herein, by employing the nitrogen-silica-doped carbon (Vulcan XC-72R) as the support, we have developed a low-loading cobalt nanocatalyst (Co/N-Si-C). The combination of such a catalyst with p-nitrobenzoic acid and molecular O2 exhibits excellent catalytic performance towards the dehydrogenative coupling of (hetero)aryl-fused 2-alkylcyclic amines with aldehydes to afford the (E)-2-alkenylazaarenes. In the reaction, effective capture of the partially dehydrogenated cyclic amine motifs appears to be the key strategy to address the issue of the chemoselectivity. The developed catalytic transformation proceeds with the merits of broad substrate scope, good functional group tolerance, high atom-efficiency, use of an earth-abundant and reusable cobalt catalyst and molecular O2 as a green oxidant, which offers an important basis for the direct conversion of inert cyclic amine units into the functional frameworks.
Iodine-Catalyzed Direct C-H Alkenylation of Azaheterocycle N-Oxides with Alkenes
Zhang, Zhenhao,Pi, Chao,Tong, Heng,Cui, Xiuling,Wu, Yangjie
supporting information, p. 440 - 443 (2017/02/10)
An efficient and regioselective alkenylation of azaheterocycle N-oxides with alkenes catalyzed by iodine under metal- and external oxidant-free reaction conditions has been developed. A variety of (E)-2-styrylazaheterocycles have been produced in moderate
Use of nitrogen-containing heterocyclic radical substituted alkene compounds
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Paragraph 0216-0218; 0259-0260, (2017/09/12)
The invention relates to new use of a series of nitrogen-containing heterocyclic radical substituted alkene compounds, and more specifically relates to use of the compounds represented by general formula a or salts thereof in bioimaging, pH value detection, biomacromolecule detection or cell microenvironment detection, wherein Z, S1, S2 and R1 are defined as the specification. The compounds are utilized as the fluorescent dye for bioimaging, fluorescent pH probe for pH value detection and/or diagnostic agent for tumor cell detection. The compounds involved in the invention have excellent imaging effect, and shows the single component multicolor property, can be used for single component multicolor imaging or conventional imaging, etc., and haves enormous application prospect in bioimaging and tumor detection. (formula a).
Direct alkenylation of 2-substituted azaarenes with carbonyls via C-H bond activation using iron-based metal-organic framework Fe3O(BPDC)3 as an efficient heterogeneous catalyst
Dang, Hang T.,Lieu, Thien N.,Truong, Thanh,Phan, Nam T.S.
, p. 237 - 245 (2016/05/19)
A porous crystalline metal-organic framework Fe3O(BPDC)3 was synthesized from the reaction of biphenyl-4,4′-dicarboxylic acid and iron(III) chloride hexahydrate by a solvothermal method in the presence of acetic acid, and was characterized by using a variety of different techniques. The Fe3O(BPDC)3 could be used as an efficient heterogeneous catalyst in the synthesis of 2-alkenylazaarenes using the direct alkenylation of 2-substituted azaarenes with carbonyls via C-H bond activation. The presence of acetic acid as a co-catalyst accelerated the transformation significantly. The Fe3O(BPDC)3 exhibited better performance in this transformation then other MOFs such as Fe3O(BDC)3, Cu2(OBA)2(BPY), Cu2(BDC)2(DABCO), Ni2(BDC)2(DABCO), Zn-MOF-74, and Cu2(NDC)2(DABCO). The Fe3O(BPDC)3 also exhibited higher catalytic activity than that of several homogeneous catalysts such as FeCl2, FeCl3, CuCl2, Zn(OAc)2, Zn(NO3)2, and Ni(OAc)2. The Fe3O(BPDC)3 catalyst could be recovered and reused several times in the synthesis of 2-alkenylazaarenes without a significant degradation in catalytic activity. To the best of our knowledge, 2-alkenylazaarenes was not previously synthesized via the direct alkenylation of 2-substituted azaarenes with carbonyls using heterogeneous catalysts.
