The reaction of active methylene compounds with carbon disulfide in the presence of arylidenemalononitriles: synthesis of 6-amino-2-(4,4-dimethyl/dihydro-2,6-dioxocyclohexylidene)-4-aryl-4H-1,3-dithiine-5-carbonitrile derivatives

Mehrabi, Hossein; Esfandiarpour, Zeinab; Davodian, Tayebeh

doi:10.1080/17415993.2017.1405959

Cited by 8 publications

(11 citation statements)

References 24 publications

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“…In summary, we succeeded in synthesizing seven novel derivatives of 6'-amino-2'-(arylidene)spiro[indeno [1,2-b]quinoxaline [1,3]dithiine]-5'-carbonitrile starting from compounds possessing active methylene group, carbon disulphide, malononitrile and multi-ring compounds containing a carbonyl group using simple process. Antimicrobial activity of these compounds was evaluated against five Gram-negative and Gram-positive pathogenic bacteria.…”

Section: Discussionmentioning

confidence: 99%

“…1 Sulfur-containing heterocyclic compounds are particularly noteworthy in organic chemistry, medicine, and biochemistry due to their structure. [2][3] Spiro heterocyclic compounds lead to the biological activity of these compounds because of the commonality of a carbon between the two rings and the lack of symmetry of these compounds due to the asymmetric nature of carbon spiro compounds. [4][5][6][7][8] Biological activities, such as promising antibacterial, antifungal, [9][10][11] anti-hyperglycemic, 12 and anti-tubercular 13 effects have been reported for spiro heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

“…[15][16][17] These compounds are most often used as a carbon protection groups for the synthesis of heterocyclic compounds. [18][19][20] In this study the new derivatives of 6'-amino-2'-(arylidene)spiro[indeno [1,2-b]quinoxaline [1,3]dithiine]-5'-carbonitrile were synthesized using compounds possessing active methylene group, carbon disulfide, malononitrile, 11H-indeno [1,2-b]quinoxalin-11-one and 1H-indene-1,2,3-trione and their biological activities such as antibacterial and antifungal activities were studied.…”

Section: Introductionmentioning

confidence: 99%

“…In our previous report, new derivatives of spiro[indoline-3,4ʹ- [1,3]dithiine] were synthesized by MgO nanoparticles. 17 In this work, the synthesis of derivatives with MgO nanoparticles was investigated but the desired result was not obtained, that could be due to the larger reactant material including 11H-indeno [1,2-b]quinoxalin-11-one than in the previous work.…”

Section: Introductionmentioning

confidence: 99%

“…Synthesis of 6'-amino-2'-(arylidene)spiro[indeno[1,2-b] quinoxaline[1,3]dithiine]-5'-carbonitrile derivatives.…”

mentioning

confidence: 99%

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Synthesis, Characterization and Antimicrobial Evaluation of Novel 6’-Amino-spiro[indeno[1,2-b] quinoxaline[1,3]dithiine]-5’-carbonitrile Derivatives

Moghaddam‐Manesh¹,

Ghazanfari²,

Sheikhhosseini³

et al. 2020

ACSi

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l,3-Dithiin with two sulfurs in its structure is a six-membered, sulfur-containing heterocyclic compound. New derivatives of 6'-amino-2'-(arylidene)spiro[indeno[1,2-b]quinoxaline[1,3]dithiine]-5'-carbonitrile were prepared by the multi-component reaction of active methylene compounds, carbon disulfide, malononitrile and multi-ring compounds containing a carbonyl group in the presence of piperidine as a catalyst at room temperature with high efficiency. The antimicrobial effects including antibacterial and antifungal effects based on inhibition zone diameter (IZD), minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC) and minimum fungicidal concentration (MFC) were studied.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Synthesis of 6'-amino-2'-(arylidene)spiro[indeno[1,2-b] quinoxaline[1,3]dithiine]-5'-carbonitrile derivatives.…”

mentioning

confidence: 99%

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Synthesis, Characterization and Antimicrobial Evaluation of Novel 6’-Amino-spiro[indeno[1,2-b] quinoxaline[1,3]dithiine]-5’-carbonitrile Derivatives

Moghaddam‐Manesh¹,

Ghazanfari²,

Sheikhhosseini³

et al. 2020

ACSi

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Introducing new method for the synthesis of polycyclic compounds containing [1,3]dithiine derivatives, with anticancer and antibacterial activities against common bacterial strains between aquatic and human

Moghaddam‐Manesh

Hosseinzadegan

2021

Journal of Heterocyclic Chem

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In this study, glycerol:potassium carbonate used as a green deep eutectic solvent, for synthesis of polycyclic compounds containing [1,3]dithiine derivatives. The antimicrobial properties of the derivatives against Lactococcus garvieae and Edwardsiella tarda were tested as bacterial strains between aquatic and human based on the minimum inhibitory concentration (MIC), the minimum lethal concentration (MBC) and inhibition zone diameter (IZD).In addition to antimicrobial properties, cytotoxicity testing was performed against MCF-7 breast cancer cells via MTT cell viability assay.

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MgO‐Nanoparticle‐Catalyzed Synthesis and Evaluation of Antimicrobial and Antioxidant Activity of New Multi‐Ring Compounds Containing Spiro[indoline‐3,4′‐[1,3]dithiine]

et al. 2019

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Multi‐component reaction indoline‐2,3‐dione derivatives, malononitrile, carbon disulfide and dimedone have led to newly synthesized 6′‐amino‐2′‐(4,4‐dimethyl‐2,6‐dioxocyclohexylidene)‐2‐oxospiro[indoline‐3,4′‐[1,3]dithiine]‐5′‐carbonitrile derivatives under acidic and base conditions with high efficiency during a simplified process. In acidic conditions, using MgO nanoparticleas as a catalyst, greater yields in shorter time was observed. The biological effects of synthetic derivatives such as antibacterial and antifungal effects based on inhibition zone diameter, minimum inhibitory concentration, minimum bactericidal concentration, minimum fungicidal concentration and antioxidant effects on DPPH free radical, have been the subject of previous studies. The results showed that some derivatives show higher antimicrobial effects compared to commercial drugs.

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The reaction of active methylene compounds with carbon disulfide in the presence of arylidenemalononitriles: synthesis of 6-amino-2-(4,4-dimethyl/dihydro-2,6-dioxocyclohexylidene)-4-aryl-4H-1,3-dithiine-5-carbonitrile derivatives

Cited by 8 publications

References 24 publications

Synthesis, Characterization and Antimicrobial Evaluation of Novel 6’-Amino-spiro[indeno[1,2-b] quinoxaline[1,3]dithiine]-5’-carbonitrile Derivatives

Synthesis, Characterization and Antimicrobial Evaluation of Novel 6’-Amino-spiro[indeno[1,2-b] quinoxaline[1,3]dithiine]-5’-carbonitrile Derivatives

Introducing new method for the synthesis of polycyclic compounds containing [1,3]dithiine derivatives, with anticancer and antibacterial activities against common bacterial strains between aquatic and human

MgO‐Nanoparticle‐Catalyzed Synthesis and Evaluation of Antimicrobial and Antioxidant Activity of New Multi‐Ring Compounds Containing Spiro[indoline‐3,4′‐[1,3]dithiine]

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