Facile synthesis of 2‐alkylthio‐3‐amino‐4 H‐imidazol‐4‐ones and 2H‐imidazo[2,1‐b]‐1,3,4‐thiadiazin‐6(7H)‐ones via N‐vinylic iminophosphorane

Ding, Ming‐Wu; Fu, Boqiao; Yuan, Jing

doi:10.1002/hc.20069

Cited by 15 publications

(4 citation statements)

References 16 publications

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“…2-Thiohydantoin derivatives have not only been used in medicinal chemistry, but have also been developed as fungicides e.g. fenamidone [ 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

New Imidazolidineiminothione, Imidazolidin-2-one and Imidazoquinoxaline Derivatives: Synthesis and Evaluation of Antibacterial and Antifungal Activities

Ammar

El‐Sharief

Ghorab

et al. 2016

COS

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A series of new 5-imino-4-thioxo-2-imidazolidinone derivatives 3 with various halogenated and alkylated aromatic substituents at N1 and N3 was synthesized. Imidazolidineiminothione derivatives 3 were prepared from the reaction of N-arylcyanothioformamide derivatives with aryl isocyanates. These compounds were used as key synthons for the preparation of wide variety of new substituted imidazole compounds. Imine hydrolysis of 3 with ethanolic HCl produced the corresponding 4-thioxo-2,5-imidazolidindiones 4. Condensation of 3 with benzophenonhydrazone furnished the corresponding 4-azine derivatives 5. Monohydrazono and dihydrazono derivatives 6 and 8 were obtained upon treatment of imidazolidinone derivatives 3 with hydrazine hydrate. Finally, imidazolidinones 3 were reacted with o-phenylenediamines or pyrazol-5(4H)-ones and afforded the corresponding imidazoquinoxaline and imidazolidin-4-ylidenepyrazolone-5(4H)-one derivatives 11 and 12, respectively. Evaluation of the antibacterial and antifungal activities for the synthesized compounds was carried out to probe their activities. Most of the tested compounds showed significant activities. The best antimicrobial activity was observed for 1-(3-ethoxyphenyl)-6-methyl-1-phenyl-1H-imidazo[4,5-b]quinoxalin-2(3H)-ones (11c) followed by 5-imino-3-(3-methoxy- phenyl)-1-phenyl-4-thioxoimidazolidin-2-one (3f).

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“…2-Thiohydantoin derivatives have not only been used in medicinal chemistry, but have also been developed as fungicides e.g. fenamidone [ 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

New Imidazolidineiminothione, Imidazolidin-2-one and Imidazoquinoxaline Derivatives: Synthesis and Evaluation of Antibacterial and Antifungal Activities

Ammar

El‐Sharief

Ghorab

et al. 2016

COS

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“…The 5-arylmethylene-2-methylthio-imidazol-4-ones III substituted with a biphenyltetrazole (BTP) group at the C-2 position show activities as angiotensin II receptor antagonists [5] and the 3-morpholinomethyl-5,5-dimethyl-2-thioglycosyl-imidazol-4-one IV has been also identified as a potential AZT analogue [6]. The 2-thiohydantoin derivatives have not only been used in medicinal chemistry, but have also been developed as fungicides [7] [e.g., fenamidone ( V) [8,9]] and herbicides [10]. Recent work [11] by Wang's group has established that esters of 5-(4-hydroxybenzyl)thiohydantoins exhibit good herbicidal activity against Zea mays and Arabidopsis thaliana .…”

Section: Introductionmentioning

confidence: 99%

A Practical Approach to New (5Z) 2-Alkylthio-5-arylmethylene-1-methyl-1,5-dihydro-4H-imidazol-4-one Derivatives

et al. 2011

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“…Intramolecular aza-Wittig reactions mainly involve phosphazenes generated by Staudinger reactions. In this context, a new efficient synthesis of thiadiazinones 92 has been recently reported by means of functionalized ketophosphazenes[31]. However, in this case phosphazenes wereprepared by Kirsanov reaction (Scheme 26) [3h].…”

mentioning

confidence: 99%

Synthetic Applications of Intramolecular Aza-Wittig Reaction for the Preparation of Heterocyclic Compounds

Palácios¹,

Aparicio²,

Rubiales³

et al. 2009

COC

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A review focused on recent advances in intramolecular aza-Wittig reaction of phosphazenes with several carbonyl or analogous compounds is reported. Phosphazenes afford intramolecular aza-Wittig reaction with different groups within the molecule as aldehydes, ketones, esters, thioesters, amides, anhydrides and sulfimides. One of the most important applications of this reaction is the synthesis of a wide range of heterocyclic compounds, ranging from simple monocyclic compounds to complex polycyclic and macrocyclic systems.

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Facile synthesis of 2‐alkylthio‐3‐amino‐4 H‐imidazol‐4‐ones and 2H‐imidazo[2,1‐b]‐1,3,4‐thiadiazin‐6(7H)‐ones via N‐vinylic iminophosphorane

Abstract: 2-Alkylthio-3-amino-4H-imidazol-4-ones 5 were synthesized by S-alkylation of 2-thioxo-3-amino-4-imidazolidinones 4, which were obtained via cyclization of isothiocyanates 2 with hydrazine hydrate. 5l-n reacted

Cited by 15 publications

References 16 publications

New Imidazolidineiminothione, Imidazolidin-2-one and Imidazoquinoxaline Derivatives: Synthesis and Evaluation of Antibacterial and Antifungal Activities

New Imidazolidineiminothione, Imidazolidin-2-one and Imidazoquinoxaline Derivatives: Synthesis and Evaluation of Antibacterial and Antifungal Activities

A Practical Approach to New (5Z) 2-Alkylthio-5-arylmethylene-1-methyl-1,5-dihydro-4H-imidazol-4-one Derivatives

Synthetic Applications of Intramolecular Aza-Wittig Reaction for the Preparation of Heterocyclic Compounds

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