Preparation of perinones via a novel multicomponent synthesis of isoindole scaffold

Üngören, Şevket Hakan; Koca, İrfan; Yılmaz, Filiz

doi:10.1016/j.tet.2011.05.078

Cited by 10 publications

(7 citation statements)

References 33 publications

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“…Based on its spectral data (MS, IR, 1 H-NMR and 13 C-NMR) the 2-(2-hydroxybenzoylmethylene)-1,2-dihydroperimidine structure 8 was assigned to the reaction product. For example, its 13 C-NMR revealed a characteristic signal at δ 186.22 due to a ketonic carbonyl-carbon rather than an amidic carbonyl-carbon where the latter one resonates in the region δ 160–166 [25] and the signal for methene carbon at 77.15 [37]. Also, the carbon signals of the perimidine moiety were clearly observed in the 13 C-NMR spectrum of compound 8 [37].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

et al. 2014

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Two series of naphtho[1,8-ef][1,4]diazepines and pyrrolo[1,2-a]perimidines were prepared starting from 1,8-diaminonaphthalene and hydrazonoyl chlorides. The structures of the products were determined on the basis of their spectral data and elemental analyses. The mechanism of formation of such products was also discussed. The prepared compounds were screened for their antitumor activity against three cell lines, namely, MCF-7, TK-10 and UACC-62, and some derivatives showed promising activity.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

et al. 2014

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“…The required starting ketene aminals 1 and 2 were prepared as previously reported 2. Reaction of 1 or 2 with diazotized aniline derivatives in aqueous ethanol in the presence of sodium acetate afforded the respective arylazo derivatives 4a–j and 5a–j (Scheme ).…”

Section: Resultsmentioning

confidence: 86%

“…Heterocyclic ketene aminals (HKAs) and hydrazonoyl halides are powerful and versatile intermediates for the synthesis of a large number of heterocyclic compounds 1–7. Several reports revealed that hydrazones are known as one of the most important classes of organic compounds, some of which possess significant biological activities, like analgesic, antitumor, anti‐inflammatory, antibacterial, and antifungal, and they also play the role of anticancer, and immunomodulating agents 8–13.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Tautomeric Structures, and Antitumor Activity of New Perimidines

Farghaly

Mahmoud

2013

Archiv der Pharmazie

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New series of perimidine derivatives and fused perimidines were derived from the reaction of ketene aminals 1 and 2 with diazotized anilines or hydrazonoyl chlorides. In addition, 8,10-disubstituted-[1,2,4]triazolo[4,3-a]perimidines (20a-m) were prepared through the reaction of perimidine-2-thione (15) with hydrazonoyl chlorides. The structures of the newly synthesized compounds were established on the basis of spectral data and elemental analyses. Some products were investigated for their antitumor activities against the human breast cancer cell line MCF-7 and the liver carcinoma cell line HEPG-2, and the results of some derivatives showed promising activity.

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“…However, 2‐(benzoylmethylene)‐1,2‐dihydro‐perimidine ( 3 ) has been previously reported from the reaction of the corresponding diketone or 3,3‐dichloro‐acryloyl chloride with 1,8‐diamino‐naphthalene . Recently , compound 3 was prepared by the reaction of 1,8‐diamino‐naphthalene 1 with ethyl benzoylacetate 2 under reflux for 6 h in xylene in the presence of P ‐toluenesulfonic acid (PTSA catalytic amount) in good yields (56–73%). In this work, we report here a new approach for the preparation of 3 .…”

Section: Resultsmentioning

confidence: 99%

Site‐ and Regioselectivity of the Reaction of Hydrazonoyl Chlorides with Perimidine Ketene Aminal. Antimicrobial Evaluation of the Products

Farghaly

Mahmoud

2014

Journal of Heterocyclic Chem

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Reaction of hydrazonoyl chlorides with perimidine ketene aminal derivative in dioxane in the presence of triethylamine afforded either pyrrolo[1,2‐a]perimidines or pyrazolyl perimidines depending on the type of hydrazonoyl chloride used. The reaction was found to be site‐ and regioselective according to the suggested mechanism. The structure of the newly synthesized compounds was established on the basis of spectral data and elemental analyses. In addition, the antimicrobial activity of the newly synthesized compounds was evaluated, and the results showed moderate activity of all compounds against the bacterial species.

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Preparation of perinones via a novel multicomponent synthesis of isoindole scaffold

Cited by 10 publications

References 33 publications

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

Synthesis, Tautomeric Structures, and Antitumor Activity of New Perimidines

Site‐ and Regioselectivity of the Reaction of Hydrazonoyl Chlorides with Perimidine Ketene Aminal. Antimicrobial Evaluation of the Products

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