Microwave assisted one pot synthesis of a series of trifluoromethyl substituted spiro [indole–triazoles]

Dandia, Anshu; Singh, Ruby; Sachdeva, Harshita; Arya, Kapil

doi:10.1016/s0022-1139(01)00429-8

Cited by 29 publications

(10 citation statements)

References 15 publications

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“…In continuation of our work to develop green methodologies for the synthesis of organic compounds [33][34][35][36], herein we wish to report a mild and highly efficient procedure for the synthesis of 3-[1-(5-amino-[1,3,4]-thiadiazol-2yl)substitutedethylimino]-5-substituted-2,3-dihydro-indol-2-one derivatives (4) using water as a green solvent and citric acid as a green catalyst (Scheme 1). 4 was synthesized by the one-pot multicomponent condensation reaction of substituted 1H-indole-2,3diones (1), various amino acids (2), and thiosemicarbazide (3) in the presence of lemon juice.…”

Section: Resultsmentioning

confidence: 99%

Green Route for Efficient Synthesis of Novel Amino Acid Schiff Bases as Potent Antibacterial and Antifungal Agents and Evaluation of Cytotoxic Effects

Sachdeva

Saroj

Khaturia

et al. 2014

Journal of Chemistry

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Green chemical one-pot multicomponent condensation reaction of substituted 1H-indole-2,3-diones (1), various amino acids (2), and thiosemicarbazide (3) is found to be catalyzed by lemon juice as natural acid using water as a green solvent to give the corresponding Schiff bases (4) in good to excellent yields. This method is experimentally simple, clean, high yielding, and green, with reduced reaction times. The product is purified by simple filtration followed by washing with water and drying process. The synthesized compounds are characterized by FT-IR,13CNMR, and1HNMR spectroscopy and are screened for their antifungal activity againstAspergillus niger,Penicillium notatum,Fusarium oxysporum,Alternaria brassicicola,Chaetomium orium, andLycopodium sp.and antibacterial activity against Gram-positive bacteria,Bacillus licheniformis,Staphylococcus aureus, andMicrococcus luteus,and Gram-negative bacteria,Pseudomonas aeruginosaandEscherichia coli. Compounds have also been evaluated for cytotoxic effects against human colon cancer cell line Colo205.

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Section: Resultsmentioning

confidence: 99%

Green Route for Efficient Synthesis of Novel Amino Acid Schiff Bases as Potent Antibacterial and Antifungal Agents and Evaluation of Cytotoxic Effects

Sachdeva

Saroj

Khaturia

et al. 2014

Journal of Chemistry

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“…Employing this type of approach, S-methyl isothioamide hydroiodides were condensed with acylhydrazides in the presence of silica gel and solid ammonium acetate in a domestic microwave instrument (Scheme 3.20) 35 . An interesting one-pot three-component synthesis of spiro-fused oxindole triazoles has been reported, which involves the condensation of substituted isatins with anilines under microwave heating, followed by cyclocondensation with thiosemicarbazide (Scheme 3.20) 36 . In this case, a dry reaction support such as Montmorillonite clay was preferable to an organic solvent.…”

Section: Five-membered Ring Systems With More Than Two Heteroatomsmentioning

confidence: 99%

Heterocyclic Chemistry Using Microwave‐Assisted Approaches

Besson

Brain

2005

Microwave Assisted Organic Synthesis

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“…For example 1,2,4-triazoles exhibit pesticidal activity. Hence it was considered that combinations of indole and 1,2,4-triazole structures might provide more potent pesticides 23 . In continuation of our studies on the synthesis and evaluation of biological activity of new heterocycles [24][25][26][27][28][29][30] , we report herein the efficient synthesis of new hydrazones, and Schiff bases based on the indole moiety and the evaluation of their biological activity as antimicrobial and anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis andin vitrobiological evaluation of new heterocycles based on the indole moiety

Kandile

Mohamed

Ismaeel

2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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New compounds based on the indole moiety were synthesized via the reaction of indole-3-carbinal 1 with different nucleophiles such as 6-aryl-[4-(2-methoxybenzyl)pyridazin-3-yl] hydrazones 2a-c, benzidine, 3,3 0 -dimethoxybenzidine 4a,b and 2,6-diaminopyridine 6 to afford hydrazine derivatives 3a-c and three different classes of bis-Schiff bases. The structures of the new compounds were elucidated on the basis of their FTIR, 1 H NMR, 13C NMR spectral data, GC/MS and elemental analysis. The antimicrobial activity of the new compounds was evaluated using a broth dilution technique in terms of minimal inhibitory concentration (MIC) against four pathogenic bacteria and two pathogenic fungi strains. Compound 14b showed excellent activity against Escherichia coli and Klebsiella pneumoniae. Some of the prepared compounds were tested for anti-cancer activity against human cell lines HCT116 (colon), MCF7 (breast) and HELA (cervix). From the results of the in vitro assays, compounds 3a,b, and 18a,c presented promising anti-cancer activity.

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Microwave assisted one pot synthesis of a series of trifluoromethyl substituted spiro [indole–triazoles]

Cited by 29 publications

References 15 publications

Green Route for Efficient Synthesis of Novel Amino Acid Schiff Bases as Potent Antibacterial and Antifungal Agents and Evaluation of Cytotoxic Effects

Green Route for Efficient Synthesis of Novel Amino Acid Schiff Bases as Potent Antibacterial and Antifungal Agents and Evaluation of Cytotoxic Effects

Heterocyclic Chemistry Using Microwave‐Assisted Approaches

Synthesis andin vitrobiological evaluation of new heterocycles based on the indole moiety

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