26964-88-5

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InChI:InChI=1/C9H6N4O2/c10-12-11-5-13-8(14)6-3-1-2-4-7(6)9(13)15/h1-4H,5H2

Upstream product

• 5332-26-3 N-(bromomethyl)phtalimide 
• 4702-13-0 N-phthaloylglycine 
• 17564-64-6 N-(chloromethyl)phthalimide 

Relevant academic research and scientific papers

Design and semisynthesis of new herbicide as 1,2,3-triazole derivatives of the natural maslinic acid

Interesting biological activities (anti-inflammatory, anticancer, antiviral, antioxidant, antidiabetic…) have been reported for maslinic acid (MA) and MA-based compounds. In continuation of our previous work on MA, herbicide potential of Tunisian plant extracts and 1,4-triazolyl derivatives of MA, we now wish to report semisynthesis of new MA-based triazole hybrid compounds with herbicide potential. These compounds were synthesized through Cu-catalyzed azide-alkyne cycloaddition (CuAAC) under microwave irradiation conditions between propargylated MA and a series of phthalimide azides. Here, the first partner of CuAAC reaction (propargylated MA) resulted from propargylation of C-28 carboxylic acid group of isolated MA from the well-known Mediterranean plant Olea europaea L. (Oleaceae). So far, phthalimide azide derivatives were achieved by trapping of N-acyliminium ion, in-situ generated under catalytic condition of Bi(OTf)3, by aromatic nucleophiles. The cycloaddition reaction afforded regiospecifically 1,4-disubstituted triazoles in good yields. The latter hybrid compounds were shown to exhibit a high inhibition potential of seed germination. This constitutes the first step in development of potent herbicides since one of the final semisynthesized structures can serve as a promising lead candidate for further studies.

Lewis acid catalyzed site-selective cycloadditions of 2,6- diazasemibullvalenes with isocyanides, azides, and diazo compounds for the synthesis of diaza- and triazabrexadiene derivatives

Unprecedented cycloaddition pathways: Lewis acid catalyzed cycloadditions of 2,6-diazasemibullvalenes with isocyanides, azides, and diazo compounds lead to structurally interesting and otherwise unavailable cage diaza- and triazabrexadiene derivatives. Un

Structure and evaluation of antibacterial and antitubercular properties of new basic and heterocyclic 3-formylrifamycin SV derivatives obtained via 'click chemistry' approach

Thirty four novel derivatives of 3-formylrifamycin SV were synthesized via reductive alkylation and copper(I)-catalysed azide-alkyne cycloaddition. According to the obtained results, 'click chemistry' can be successfully applied for modification of struct

1,4- and 1,5-di(N-phthalimidomethyl)-1,2,3-triazoles: Crystal structures and density functional theory studies of the alkyne and azide precursors

Two new di(phthalimidomethyl)-1,2,3-triazole derivatives have been synthesised using 1,3-dipolar-cycloadditions under thermal and copper catalysed conditions from N-(azidomethyl)phthalimide and N-prop-2-ynylphthalimide. The molecular structure of both starting materials was studied by X-ray crystallography. A complete DFT analysis of the alkyne and azide compounds was carried out.

Design and Synthesis of Triazole-Phthalimide Hybrids with Anti-inflammatory Activity

Phthalimido-alkyl-1H-1,2,3-triazole derivatives 3a–d and 4a–d were efficiently synthesized using 1,3-di-polar cycloaddition reaction. Anti-inflammatory activity and toxicity studies were performed. The results demonstrated that all the tested compounds reduced carrageenan-induced paw edema and indicated no lethality for toxicity against Artemia salina and acute toxicity in vivo (LD50 up to 1gkg ?1). Furthermore, the structure of phthalimide linked to phenyl group proved to be more active than the compounds containing benzothiazole moiety. Structural modifications such as removal of the phthalimide group and subsequent acetylation, to exemplify a non-cyclic amide, demonstrate that the phthalimide and triazole moieties are important for design of potent candidates with anti-inflammatory drug proprieties. Docking into the cyclooxy-genase-2 (COX-2) confirms the importance of the phthalimide and triazole groups in the anti-inflammatory activity. The histopathological studies showed that the compounds 3a–d and 4a–d did not cause serious pathological lesions liver or kidneys.

Silver-Catalyzed Decarboxylative Azidation of Aliphatic Carboxylic Acids

The catalytic decarboxylative nitrogenation of aliphatic carboxylic acids for the synthesis of alkyl azides is reported. A series of tertiary, secondary, and primary organoazides were prepared from easily available aliphatic carboxylic acids by using K2S2O8 as the oxidant and PhSO2N3 as the nitrogen source. The EPR experiment sufficiently proved that an alkyl radical process was generated in the process, and DFT calculations further supported the SET process followed by a stepwise SH2 reaction to afford azide product.

Efficient one-pot synthesis of 1,2,3-triazoles from benzyl and alkyl halides

An efficient one-pot method for the preparation of 1,2,3-triazoles by 1,3-dipolar cycloaddition of in situ generated azides and alkynes is presented. This facile method can be applied to benzyl or alkyl halides and pure products are isolated by simple filtration.