New synthetic “tricks” One-pot preparation of N-substituted phthalimides from azides and phthalic anhydride

García, Jordi; Vilarrasa, Jaume; Bordas, Xavier; Banaszek, Anna

doi:10.1016/s0040-4039(00)84061-7

Cited by 40 publications

(28 citation statements)

References 8 publications

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“…The utilization of carboxylic esters leads to compounds containing an acid amide bond between the organic moiety of the former azide and the organic residue of the former ester after hydrolysis of the intermediate. Thus, this intermolecular variant of the Staudinger ligation (three‐component‐reaction) was applied in the past for conjugation purposes . Both reaction mechanisms are illustrated in Scheme .…”

Section: Origin Of the Staudinger Ligationmentioning

confidence: 99%

Recent progress using the Staudinger ligation for radiolabeling applications

Mamat

Gott

Steinbach

2018

Labelled Comp Radiopharmac

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The increasing application of positron emission tomography and single-photon emission computer tomography in radiopharmacy and nuclear medicine has stimulated the development of a multitude of novel and versatile bioorthogonal conjugation techniques. Currently, there is particular interest in radiolabeling biologically active, high molecular weight compounds like peptides, proteins, or antibodies, but also for the labeling of small organic compounds. An enormous challenge in radiolabeling these biologically active molecules is that the introduction of radiohalogens like fluorine-18 as well as various radiometals proceeds under harsh conditions, which could destroy the biomolecule. The Staudinger ligation is one of the most powerful bioorthogonal conjugation techniques. The reaction proceeds over wide temperature and pH ranges; an amide (peptide) bond is formed as the ligation unit, which minimizes distortion of the structure; no isomers are obtained; and the reaction proceeds without any metal catalyst. Due to this adaptability, this robust ligation type is a perfect candidate with a high potential for various applications in the field of radiopharmacy for the labeling of biomolecules under mild conditions. This review summarizes recent research concerning the implementation of the Staudinger ligation for radiolabeling applications.

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Section: Origin Of the Staudinger Ligationmentioning

confidence: 99%

Recent progress using the Staudinger ligation for radiolabeling applications

Mamat

Gott

Steinbach

2018

Labelled Comp Radiopharmac

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“…Instead, we applied the direct Staudinger reduction/acylation protocol of Vilarassa and coworkers, which allows the direct conversion of an azide to an amide without the intermediacy of an amine. [21] Depending on the order of addition of reagents, this process proceeds via either an iminophosphorane or a triazaphosphadiene/acyl chloride adduct. [22] Accordingly, 23 was subjected to PPh 3 and AcCl to afford the acetamide 24 in a 64 % yield.…”

Section: Synthesis Of Sulfated Substratesmentioning

confidence: 99%

Synthesis of Sulfated Glucosaminides for Profiling Substrate Specificities of Sulfatases and Fungal β‐N‐Acetylhexosaminidases

et al. 2009

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Systematic sulfation: Sulfated glycoconjugates are degraded either by desulfation followed by glycoside cleavage, or by glycoside cleavage followed by desulfation. To study these processes, here we report the synthesis of four regioisomerically sulfated p-nitrophenyl glucosaminides from the common precursor p-nitrophenyl N-acetyl-beta-D-glucosaminide. These substrates allowed the rapid analysis of the substrate preferences of a set of four sulfatases and 24 hexosaminidases.Sulfated carbohydrates are components of many glycoconjugates, and are degraded by two major processes: cleavage of the sulfate ester by a sulfatase, or en bloc removal of a sulfated monosaccharide by a glycoside hydrolase. However, these processes have proved difficult to study owing to a lack of homogeneous, defined substrates. We describe here the synthesis of a series of p-nitrophenyl beta-D-glucosaminides bearing sulfate esters at the 2-, 3-, 4- or 6-positions, by divergent routes starting with p-nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside. The sulfated p-nitrophenyl beta-D-glucosaminides were used to study the substrate specificity of four sulfatases (from Helix pomatia, Patella vulgata, abalone, and Pseudomonas aeruginosa), and revealed significant differences in the preference of each of these enzymes for desulfation at different positions around the sugar ring. The 3-, 4- and 6-sulfated p-nitrophenyl 2-acetamido-2-deoxy-beta-D-glucosaminides were screened against a panel of 24 fungal beta-N-acetylhexosaminidases to assess their substrate specificity. While the 4- and 6-sulfates were substrates for many of the fungal enzymes investigated, only a single beta-N-acetylhexosaminidase, that from Penicillium chrysogenum, could hydrolyze the 3-sulfated p-nitrophenyl glycoside. Together these results demonstrate the utility of sulfated p-nitrophenyl beta-D-glucosaminides for the study of both sulfatases and glycoside hydrolases.

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“…According to this reaction mechanism, the condensation reaction proceeds with a virtually complete configuration inversion. This accounts for the different behaviour observed between 9-methyl-9-azabicyclo[3.3.1]nonan-3α and β-ols (13,12) and between 8-methyl-8-azabicyclo[3.2.1]octan-3α and β-ols (10,11). In this case, starting from 3-α-tropanol (10) the β-phthalimide (2) was obtained as a result of an S2N type displacement in the oxyphosphonium salt.…”

Section: Chemistrymentioning

confidence: 92%

“…Phthalimides are directly obtained from these general methods, but they have also been obtained from a number of unusual starting materials and methods [3][4][5][6][12][13][14][15][16]. The reaction of potassium phthalimide with halogenoalkanes and with a variety of other alkylating agents leads to N-alkylphthalimide.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural and conformational study of selected N-substituted phthalimides

et al. 2005

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This paper synthesizes N -substituted phthalimides derived from nitrogen heterocycles as potential 5-HT 4 ligands by using the Mitsunobu reaction. Conformational studies of some of the new compounds have been conducted using 1 H and 13 C-NMR spectroscopy. Proton and carbon resonances were achieved through the application of onedimensional selective NOE, two-dimensional NMR techniques -homonuclear COSY-45, NOESY and heteronuclear 1 H-13 C HMQC correlated spectroscopy-and double resonance experiments. The crystal structure of compound 1 was determined by X-ray diffraction.

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New synthetic “tricks” One-pot preparation of N-substituted phthalimides from azides and phthalic anhydride

Cited by 40 publications

References 8 publications

Recent progress using the Staudinger ligation for radiolabeling applications

Recent progress using the Staudinger ligation for radiolabeling applications

Synthesis of Sulfated Glucosaminides for Profiling Substrate Specificities of Sulfatases and Fungal β‐N‐Acetylhexosaminidases

Synthesis, structural and conformational study of selected N-substituted phthalimides

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