Synthese von Pyrrolderivaten: Pyrrole aus Succinylobernsteinsäureester, Pyrrole aus Azinen

Piloty, O.

doi:10.1002/cber.19100430182

Cited by 77 publications

(13 citation statements)

References 11 publications

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“…Classical methods for the synthesis of pyrroles are Piloty [36] Paal-Knorr [37,38], Barton-Zard [39], and Hantzsch [40], syntheses. Nowadays, new approaches involving the use of transition-metal intermediates [41], multicomponent reactions [42], and reductive couplings [43] are documented.…”

Section: Introductionmentioning

confidence: 99%

Facile and sustainable functionalization of graphene layers with pyrrole compounds

Barbera

Bernardi

Palazzolo

et al. 2017

Pure and Applied Chemistry

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A facile and sustainable functionalization of graphene layers was performed with pyrrole compounds (PyC) prepared through the Paal-Knorr reaction of a primary amine with 2,5-hexanedione. A good number of primary amines were used: hexanamine, dodecanamine, octadecanamine, 2-aminoacetic acid, 2-amino-1,3-propanediol, 3-(triethoxysilyl)propan-1-amine. The reactions were characterized by good yield, up to 96 %, and indeed satisfactory atom efficiency, up to 80 %. The functionalization of graphene layers was obtained by mixing PyC with a high surface area graphite and heating at a temperature range from 130 °C to 150 °C for 3 h. The yield of functionalization reaction was larger than 60 % and also up to about 90 % for the pyrrole compounds from dodecanamine and 2-amino-1,3-propanediol, respectively. The cycloaddition reaction between the graphene layers and the pyrrole compound, oxidized in two position, is proposed as working hypothesis to account for such efficient functionalization. Raman spectroscopy revealed that the structure of the graphitic substrate remained substantially unaltered, after the reaction. Stable dispersions of HSAG adducts with different PyC were prepared in solvents with different solubility parameters and HRTEM analysis showed the presence of aggregates of only few layers of graphene. Qualitative results of dispersion tests were used to calculate the Hansen sphere for the HSAG adduct with the pyrrole compound based on dodecanamine so to provide a first estimate of its Hansen solubility parameters. This work paves the way for the facile and sustainable modification of the solubility parameters of graphene layers and for the predictive assessment of their compatibility with different environments.

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Section: Introductionmentioning

confidence: 99%

Facile and sustainable functionalization of graphene layers with pyrrole compounds

Barbera

Bernardi

Palazzolo

et al. 2017

Pure and Applied Chemistry

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“…13 C-NMR: 9.6 (Me); 10.1 (Me); 28.3 (3 Me); 28.4 (3 Me); 80.7 (C); 81.2 (C); 116.9 (C(4)); 119.9 (C(2)); 122.7 (C(3)); 128.6 (C(5)); 160.0 (C(2)ÀCO); 164.9 (C(3)ÀCO). EI-MS: 295 (3), 240 (2), 183 (21) …”

Section: Methodsmentioning

confidence: 99%

One‐Pot Four‐Component Synthesis of Tetrasubstituted Pyrroles

Kassaee

Masrouri

Movahedi

et al. 2008

Helvetica Chimica Acta

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A convenient one-pot four-component synthesis of tetrasubstituted pyrroles was carried out through the reaction of butane-2,3-dione with a-aminophosphorous ylides, obtained in situ from the 1 : 1 : 1 addition reaction between triphenylphosphine, dialkyl acetylenedicarboxylate, and ammonium acetate.Introduction. -One-pot multicomponent processes combine principles of synthetic efficiency and reaction design, while attracting considerable academic, economic, and ecological interests , and many other syntheses [22] have been used to produce this valuable heterocycle.As part of our current studies on the development of new routes in heterocyclic synthesis [23], we report a simple one-pot multicomponent synthesis of 1H-pyrrole-2,3-dicarboxylate.

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“…The largely neglected Piloty-Robinson [720][721][722] pyrrole synthesis has been adapted to microwave conditions [723], providing a route to 3,4-dialkylpyrroles, in particular 3,4-diethylpyrrole, a building block for construction of octaethylporpyrins [724,725]. Thus, the intermediate azine 474 was generated by exposure of butyraldehyde to hydrazine hydrate in diethyl ether.…”

Section: Addendummentioning

confidence: 99%