Synthesis of Imidazo[1,2‐<i>a</i>]pyridines and Imidazo[2,1‐<i>b</i>]thiazoles Attached to a Cycloalkyl or Saturated Heterocycle Containing a Tertiary Hydroxy Substitution

Reddy, M. L. Chenna; Patil, Vineetkumar B.; Khan, Fazlur-Rahman Nawaz; Saravanan, Vadivelu

doi:10.1002/jhet.3454

Cited by 9 publications

(3 citation statements)

References 49 publications

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“…The spatial structure of 5,6-dihydroimidazo[2,1- b ]thiazole analogues provides additional insights into its binding ability with bovine serum albumin (BSA) . Traditional protocols for the synthesis of imidazo[2,1- b ]thiazoles involve the cyclo-condensation of 2-mercaptoimidazoles or 2-aminothiazoles with various compounds such as 1,3-dicarbonyl, α-halocarbonyl compounds, bromohydroxycycloalkyl ethanones, N -(2,2-dichloro-2-phenylethylidene)arenesulfonamides, and N -sulfonylphenyldichloroacetaldimines . Other protocols involve a multicomponent assemblage of isocyanide, aldehyde, and 2-aminothiazole, also referred to as Groebke-Blackburn-Bienayme reaction (GBBR) …”

Section: Introductionmentioning

confidence: 99%

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

et al. 2022

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Fused heterocyclic systems containing a bridgehead nitrogen atom have emerged as imperative pharmacophores in the design and development of new drugs. Among these heterocyclic moieties, the imidazothiazole scaffold has long been used in medicinal chemistry for the treatment of various diseases. In this study, we have established a simplistic and environmentally safe regioselective protocol for the synthesis of 5,6-dihydroimidazo[2,1-b]thiazole derivatives from easily available reactants. The reaction proceeds through in situ formation of the α-bromodiketones ensuing trap with imidazolidine-2-thione to provide these versatile bicyclic heterocycles in excellent yields. The synthesized compounds were screened through the molecular docking approach for the most stable complex formation with bovine serum albumin (BSA) and calf thymus deoxyribonucleic acid (ctDNA). The selected compound was further studied using ex vivo binding studies, which revealed moderate interactions with BSA and ctDNA. The binding studies were performed using biophysical approaches including UV–visible spectroscopy, steady-state fluorescence, circular dichroism (CD), and viscosity parameters.

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Section: Introductionmentioning

confidence: 99%

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

et al. 2022

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“…Interestingly, a three‐component reaction of aryl glyoxal, 2‐aminobenzothiazole, and 1,3‐dicarbonyls in the presence of lemon juice was recently reported for the synthesis of benzo[ d ]imidazo[2,1‐ b ]thiazoles [35]. For the synthesis of benzo[ d ]imidazo[2,1‐ b ]thiazole derivatives, number of catalytic techniques have been envisaged as utilizing the NaHCO 3 [36], Cu(OAc) 2 .H 2 O [37], Cu(OAc) 2 /Cs 2 CO 3 [38], Cs 2 CO 3 [39] and Cu(OTf) 2 [40].…”

Section: Introductionmentioning

confidence: 99%

Catalyst‐free, one‐pot three‐component synthesis of N,3‐diphenybenzo[d]imidazo[2,1‐b]thiazoles and oxybis(1‐phenyl‐2‐(phenylamino)ethanones)

Hajipour

Mehrabi

2023

Journal of Heterocyclic Chem

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The present work, highlights a highly effective unique procedure for the synthesis of N,3diphenybenzo[d]imidazo[2,1-b]thiazoles and oxybis(1-phenyl-2-(phenylamino)ethanones via the one-pot three-component reaction between aryl glyoxal, aryl amine, and 2-aminobenzothiazole under catalyst-free conditions. The present mild and green method uses EtOH without catalyst at re ux conditions. No catalyst with high yields, availability of the starting materials, operational simplicity, cleaner reaction pro le, no harmful by-products, and the isolated products in pure form are the advantages of this protocol. Structures of all the freshly synthesized products have been deduced by their FT-IR, 1 H-NMR, 13 C-NMR, and elemental analysis.

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“…Literature survey revealed that in recent years assorted transition-metals catalyzed reactions have been reported as a cornerstone for the synthesis of these fused tricyclic heterocyclic core nuclei. A number of catalytic techniques have been envisaged as utilizing the CuOTfÁC 6 H 6 /Cu(OTf) 2 , [10] NaHCO 3 , [11] Cu(OAc) 2 .H 2 O, [12] FeCl 3 /ZnI 2 , [13] Cu(OAc) 2 /Cs 2 CO 3 , [14] CuI, [15] FeCl 3 , [16] Cs 2 CO 3 , [17] I 2 , [18] and Cu(OTf) 2 [19] for the systematic synthesis of these imidazo fused benzothiazole moieties. Although, it was discerned that these accounted methods abide some drawbacks comprises the use of exorbitant, moisture-sensitive reagents, ample reaction time, fatiguing workup procedures, a nonrecyclable and larger amount of catalyst loadings that leads to the production of an immense amount of environmental waste.…”

Section: Introductionmentioning

confidence: 99%

Multiwalled carbon nanotubes crowned with nickel‐ferrite magnetic nanoparticles assisted heterogeneous catalytic strategy for the synthesis of benzo[d]imidazo[2,1‐b]thiazole scaffolds

Geedkar

Kumar

Sharma

2020

Journal of Heterocyclic Chem

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Present manuscript elicits an account of the sonication promoted multicomponent reactions strategy assisted by multiwalled carbon nanotubes embraced with nickel-ferrite (NiFe 2 O 4-CNTs) magnetic nanoparticles, as a heterogeneous catalyst to synthesize a novel series of pharmacologically active benzo[d]imidazo[2,1-b]thiazole scaffolds. The synthesis of these biologically active derivatives was achieved via. A 3 coupling involving 2-aminoben zothiazole, pertinent aryl aldehydes and phenyl acetylene derivatives, proceeded in PEG 400 as green solvent under aerobic conditions to afford the products in good to excellent yields. The higher environmental compatibility and sustainability factors such as higher ecoscale score, smaller E-factor and appreciable atom economy put this etiquette under the parasol of green chemistry precepts. The characterization of synthesized catalysts was attained through varied techniques viz. powder X-ray diffraction, field emission scanning electron microscopy with energy-dispersive X-ray spectroscopy, Raman, FT-IR, VSM and TGA-DTA-DTG analyses, dispersion studies, and nitrogen porosimetry analyses. The structures of the synthesized compounds were also endorsed by extensive spectroscopic studies (FT-IR, 1 H and 13 C NMR, Mass) and elemental analyses.

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Synthesis of Imidazo[1,2‐a]pyridines and Imidazo[2,1‐b]thiazoles Attached to a Cycloalkyl or Saturated Heterocycle Containing a Tertiary Hydroxy Substitution

Cited by 9 publications

References 49 publications

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

Catalyst‐free, one‐pot three‐component synthesis of N,3‐diphenybenzo[d]imidazo[2,1‐b]thiazoles and oxybis(1‐phenyl‐2‐(phenylamino)ethanones)

Multiwalled carbon nanotubes crowned with nickel‐ferrite magnetic nanoparticles assisted heterogeneous catalytic strategy for the synthesis of benzo[d]imidazo[2,1‐b]thiazole scaffolds

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