Ciprofloxacin-functionalized magnetic silica nanoparticles: as a reusable catalyst for the synthesis of 1H-chromeno[2,3-d]pyrimidine-5-carboxamides and imidazo[1,2-a]pyridines

Soleimani, Ebrahim; Torkaman, Sara; Sepahvand, Heshmatollah; Ghorbani, Somayeh

doi:10.1007/s11030-018-9907-3

Cited by 19 publications

(10 citation statements)

References 28 publications

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“…类似地, 含叁键的化合物如腈 [37] 或异腈 [38] , 亦能作为 2-氨基吡啶 1、芳香醛 9 三组分反应体系的另一底物发生成环反应. 例如, Thennarasu 课题组 [39] [40][41] , 产率均在 70%以上.…”

Section: 以醛为原料unclassified

Application of 2-Aminopyridines in the Synthesis of Five- and Six-Membered Azaheterocycles

Chen¹,

Chen²,

Wu³

et al. 2021

Chinese Journal of Organic Chemistry

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2-Aminopyridine is a significant synthetic synthon, with unique dual nucleophilic structure. It can react with ketones, aldehydes, acids, multifunctional esters, halogenated aromatics and other compounds to synthesize five-and six-member azaheterocycles. In recent years, the cyclization reactions based on 2-aminopyridines have been under the spotlight. According to the different types of substrates, the research progress on the synthesis of imidazo[1,2-a]pyridines and pyrido[1,2-a]pyrimidines based on 2-aminopyridines in the past 5 years is reviewed, and its applications in organic synthesis methodology, drug synthesis and fluorescent probes are summarized. Furthermore, the development trend of green cyclization and its application based on 2-aminopyridines in the future are prospected. Keywords 2-aminopyridine; imidazo[1,2-a]pyridine; pyrido[1,2-a]pyrimidine; azaheterocycle; C-N bond formation; retrosynthetic analysis 吡啶环上氮原子具有较强的吸电子效应, 且吡啶 α 位基团具有特殊的作用, 使吡啶 α 位的衍生物作为合成子或中间体在有机合成、药物合成中日益引人瞩目 [1][2][3] . 其中, 2-氨基吡啶作为最典型的一种, 因其独特的双亲核结构特点为人们所重视 [4] , 特别是基于吡啶环上的氮与氨基的成环反应倍受关注 [5][6][7] .

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Section: 以醛为原料unclassified

Application of 2-Aminopyridines in the Synthesis of Five- and Six-Membered Azaheterocycles

Chen¹,

Chen²,

Wu³

et al. 2021

Chinese Journal of Organic Chemistry

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“…Apart from being commonly involved in N‐alkylation/O‐alkylation, halo FSs also take part in the formation of ionic liquids (ILs), quaternary ammonium salts and N‐heterocyclic carbene ligands. Scheme illustrates the recently reported N‐alkylation of chloro FSs with different amines (biurea, thiosemicarbazide, creatinine, 2‐amino‐3‐hydroxy‐pyridine, p‐phenylenediamine, dithiooxamide, glucosamine, melamine, 2‐amino‐2‐methyl‐1,3‐propanediol, isoniazide, adenine, urea, S‐benzylisothiourea, ethylenediamine, diethylenetriamine, o‐phenylenediamine, sulfaguanidine, sulfadiazine, ciprofloxacin, 2‐imidazolidinethion, tetramethylguanidine, and bis(2‐chloroethyl)amine hydrochloride). Enzymes like L‐asparaginase and metal complexes like manganese(II) porphyrin can be also grafted on chloro FS through N‐alkylation A cyclodextrin system is functionalized using N‐[3‐(trimethoxysilyl)propyl]ethylenediamine and subsequently subjected to N‐alkylation with chloro FS …”

Section: Conventional Fss: Types and Their Chemical Modificationsmentioning

confidence: 99%

“…In addition to their uses for the immobilization of enzymes, FSs are found very useful in immobilizing other bio‐related molecules. Succinctly explaining, amino glucose, ciprofloxacin, DL‐alanine, theophylline, cytosine, L‐serine, and (−)‐riboflavin are immobilized on FSs and utilized as the catalysts in the synthesis of different chemicals, condensation reactions, and photocatalytic E‐Z isomerization of polarized alkenes …”

Section: Applications and Advantages Of Fs‐based Catalystsmentioning

confidence: 99%

Functionalized Silicas for Metal‐Free and Metal‐Based Catalytic Applications: A Review in Perspective of Green Chemistry

Antony

Marimuthu

Yang

et al. 2019

The Chemical Record

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Heterogeneous catalysis plays a key role in promoting green chemistry through many routes. The functionalizable reactive silanols highlight silica as a beguiling support for the preparation of heterogeneous catalysts. Metal active sites anchored on functionalized silica (FS) usually demonstrate the better dispersion and stability due to their firm chemical interaction with FSs. Having certain functional groups in structure, FSs can act as the useful catalysts for few organic reactions even without the need of metal active sites which are termed as the covetous reusable organocatalysts. Magnetic FSs have laid the platform where the effortless recovery of catalysts is realized just using an external magnet, resulting in the simplified reaction procedure. Using FSs of multiple functional groups, we can envisage the shortened reaction pathway and, reduced chemical uses and chemical wastes. Unstable bio‐molecules like enzymes have been stabilized when they get chemically anchored on FSs. The resultant solid bio‐catalysts exhibited very good reusability in many catalytic reactions. Getting provoked from the green chemistry aspects and benefits of FS‐based catalysts, we confer the recent literature and progress focusing on the significance of FSs in heterogeneous catalysis. This review covers the preparative methods, types and catalytic applications of FSs. A special emphasis is given to the metal‐free FS catalysts, multiple FS‐based catalysts and magnetic FSs. Through this review, we presume that the contribution of FSs to green chemistry can be well understood. The future perspective of FSs and the improvements still required for implementing FS‐based catalysts in practical applications have been narrated at the end of this review.

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“…The surface properties such as charged/adsorbed entities [39], acidic and basic characteristics [40,41], tendency of cations to undergo redox reactions [42], and oxygen vacancies all contribute to their catalytic activity [43]. To date, Fe 3 O 4 magnetic nanoparticles (MNPs) have attracted significant interest because of their high surface reactivity and facile recovery and recycling [44][45][46][47][48][49][50].…”

Section: Introductionmentioning

confidence: 99%

Ionic liquid as an effective green media for the synthesis of (5Z, 8Z)-7H-pyrido[2,3-d]azepine derivatives and recycable Fe3O4/TiO2/multi-wall cabon nanotubes magnetic nanocomposites as high performance organometallic nanocatalyst

et al. 2021

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In this research we investigated the preparation of new (5Z, 8Z)-7H-pyrido [2,3-d]azepine derivatives in high yields via multicomponent reaction of isatins, alkyl bromides, activated acetylenic compounds and ammonium acetate using ionic liquid 1-octhyl-3-methyl imidazolium bromide ([OMIM]Br) as a stabilizer and soft template at room temperature in the presence of Fe 3 O 4 /TiO 2 /Carbon nanotubes magnetic nanocomposites as a reusable and effective nanocatalyst that are synthesized using ionic liquid [OMIM]Br as a stabilizer, soft template, green media and moderate base. Because of having a NH group in the synthesized pyridine derivatives, we investigate antioxidant property of some synthesized compounds by diphenylpicrylhydrazine (DPPH) radical trapping and power of ferric reduction experiment. Short time of reaction, high yields of product, easy separation of catalyst and products are some advantages of this procedure.

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Ciprofloxacin-functionalized magnetic silica nanoparticles: as a reusable catalyst for the synthesis of 1H-chromeno[2,3-d]pyrimidine-5-carboxamides and imidazo[1,2-a]pyridines

Cited by 19 publications

References 28 publications

Application of 2-Aminopyridines in the Synthesis of Five- and Six-Membered Azaheterocycles

Application of 2-Aminopyridines in the Synthesis of Five- and Six-Membered Azaheterocycles

Functionalized Silicas for Metal‐Free and Metal‐Based Catalytic Applications: A Review in Perspective of Green Chemistry

Ionic liquid as an effective green media for the synthesis of (5Z, 8Z)-7H-pyrido[2,3-d]azepine derivatives and recycable Fe3O4/TiO2/multi-wall cabon nanotubes magnetic nanocomposites as high performance organometallic nanocatalyst

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