1,3-Dipolar cycloaddition to the Fe-N:C fragment. 11. Isocyanide-controlled change between a reversible molecular self-assembly of three components, including a unique isocyanide deinsertion, and dimethyl maleate coupling reactions

1993 ◽  
Vol 12 (2) ◽  
pp. 440-453 ◽  
Author(s):  
Paul P. M. De Lange ◽  
Rene P. De Boer ◽  
Maarten Van Wijnkoop ◽  
Jan M. Ernsting ◽  
Hans Werner Fruhauf ◽  
...  
Keyword(s):  
Self Assembly ◽  
Dipolar Cycloaddition ◽  
Coupling Reactions ◽  
Dimethyl Maleate ◽  
Three Components

Synthesis and crystal structures of three novel benzimidazole/benzoindolizine hybrids

2016 ◽  
Vol 71 (3) ◽  
pp. 231-239 ◽  
Author(s):  
Roumaissa Belguedj ◽  
Sofiane Bouacida ◽  
Hocine Merazig ◽  
Ali Belfaitah ◽  
Aissa Chibani ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Crystal Structures ◽  
Dipolar Cycloaddition ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray ◽  
X Ray Crystallography ◽  
Dimethyl Maleate

AbstractThree benzoindolizine derivatives, 1, 2, and 3, were obtained via 1,3-dipolar cycloaddition. The reaction of 1-(2′-benzimidazolylmethyl)isoquinolinium ylides with dimethyl acetylenedicarboxylate gave a mixture of pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (1) and 1,10b-dihydropyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (2) derivatives containing a benzimidazole moiety. The reaction of this isoquinolinium N-ylide with dimethyl maleate gave an unexpected 2,3-dihydropyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate (3). The structures of all reported compounds have been examined by X-ray crystallography, mass spectrometry, and NMR spectroscopy.

Highly Diastereoselective 1,3-Dipolar Cycloaddition of a d-Galactose-Derived Nitrone with Dimethyl Maleate: Synthesis of Polyhydroxylated Perhydroaza­azulenes

Synlett ◽  
2009 ◽  
Vol 2009 (12) ◽  
pp. 1959-1963
Author(s):  
Dilip Dhavale ◽  
Omprakash Bande ◽  
Vrushali Jadhav ◽  
Vedavati Puranik
Keyword(s):  
Dipolar Cycloaddition ◽  
Dimethyl Maleate

scholarly journals Investigation of the Reactivity of 1-Azido-3-Iodobicyclo[1.1.1]pentane under “Click” Reaction Conditions

2020 ◽  
Author(s):  
Elisabeth Sitte ◽  
Brendan Twamley ◽  
nitika grover ◽  
Mathias Senge
Keyword(s):  
Click Reaction ◽  
Chemical Properties ◽  
Building Blocks ◽  
Dipolar Cycloaddition ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
Click Reactions ◽  
Drug Molecules ◽  
Physical And Chemical

The bicyclo[1.1.1]pentane (BCP) unit exhibits special physical and chemical properties and is under scrutiny as a bioisostere in drug molecules. We employed methodologies for the synthesis of different BCP triazole building blocks from one precursor, 1-azido-3-iodobicyclo[1.1.1]pentane, by Cu(I)-catalyzed 1,3-dipolar cycloaddition (“click”) reactions and integrated cycloaddition-Sonogashira coupling reactions. Thereby, we accessed three classes of substituted BCP derivatives: 1,4-disubstituted triazoles, 5-iodo-1,4,5-trisubstituted triazoles and 5-alkynylated 1,4,5-trisubstituted triazoles. This gives entry to the synthesis of multiply substituted BCP triazoles either on a modular or a one-pot basis. These methodologies were further utilized for appending large chromophoric porphyrin moieties onto the BCP core.

scholarly journals The structure and coordinative self-assembly of films based on a palladium compound of pyridyl-acetylene platinum and its application in Suzuki and Heck coupling reactions

2013 ◽  
Vol 1 (32) ◽  
pp. 9164 ◽  
Author(s):  
Xing Li ◽  
Xiuhua Zhao ◽  
Shuiying Gao ◽  
Santiago Marqués-González ◽  
Dmitry S. Yufit ◽  
...  
Keyword(s):  
Self Assembly ◽  
Coupling Reactions ◽  
Heck Coupling

Self-assembly of T-shape 2H-benzo[d][1,2,3]-triazoles. Optical waveguide and photophysical properties

RSC Advances ◽  
2016 ◽  
Vol 6 (43) ◽  
pp. 36544-36553 ◽  
Author(s):  
I. Torres ◽  
J. R. Carrillo ◽  
A. Díaz-Ortiz ◽  
R. Martín ◽  
M. V. Gómez ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Optical Waveguide ◽  
Self Assembly ◽  
Photophysical Properties ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Triazole Derivatives

T-Shaped 2H-benzo[d][1,2,3]triazole derivatives have been synthesized by Sonogashira coupling reactions under microwave irradiation.

scholarly journals Triterpenoid–PEG Ribbons Targeting Selectivity in Pharmacological Effects

Biomedicines ◽  
2021 ◽  
Vol 9 (8) ◽  
pp. 951
Author(s):  
Zulal Özdemir ◽  
Uladzimir Bildziukevich ◽  
Martina Čapková ◽  
Petra Lovecká ◽  
Lucie Rárová ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Cancer Cell ◽  
Self Assembly ◽  
Cancer Cell Line ◽  
Triazole Ring ◽  
Physicochemical Characteristics ◽  
Dipolar Cycloaddition ◽  
Pharmacological Effects ◽  
Melanoma Cancer ◽  
Positive Results

(1) Background: To compare the effect of selected triterpenoids with their structurally resembling derivatives, designing of the molecular ribbons was targeted to develop compounds with selectivity in their pharmacological effects. (2) Methods: In the synthetic procedures, Huisgen 1,3-dipolar cycloaddition was applied as a key synthetic step for introducing a 1,2,3-triazole ring as a part of a junction unit in the molecular ribbons. (3) Results: The antimicrobial activity, antiviral activity, and cytotoxicity of the prepared compounds were studied. Most of the molecular ribbons showed antimicrobial activity, especially on Staphylococcus aureus, Pseudomonas aeruginosa, and Enterococcus faecalis, with a 50–90% inhibition effect (c = 25 µg·mL−1). No target compound was effective against HSV-1, but 8a displayed activity against HIV-1 (EC50 = 50.6 ± 7.8 µM). Cytotoxicity was tested on several cancer cell lines, and 6d showed cytotoxicity in the malignant melanoma cancer cell line (G-361; IC50 = 20.0 ± 0.6 µM). Physicochemical characteristics of the prepared compounds were investigated, namely a formation of supramolecular gels and a self-assembly potential in general, with positive results achieved with several target compounds. (4) Conclusions: Several compounds of a series of triterpenoid molecular ribbons showed better pharmacological profiles than the parent compounds and displayed certain selectivity in their effects.

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