Recent advances in the synthesis of pyrroles by multicomponent reactions

Estévez, Verónica; Villacampa, Mercedes; Menéndez, J. Carlos

doi:10.1039/c3cs60015g

Cited by 662 publications

(232 citation statements)

References 109 publications

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“…ΔE cis/trans of the N-H moieties (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) range from 1.06 to 5.15, whereas those of the N-CH 3 moieties [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] range from 1.93 to 8.08 kcal/mol. The lowest energy difference bacteria [9][10][11]. There are also certain marine natural products such as nakamuric acid [12], marinopyrroles [13,14] or storniamide which show potent activity as inhibitors of multidrug resistance (MDR) [15] or pentabromopseudodiline [9] which shows good activity against some Staphylococcus aureus strains.…”

Section: Introductionmentioning

confidence: 99%

Conformational Preferences of 2-Acylpyrroles in Light of FT-IR and DFT Studies

Dubis

2014

J Phys Chem Biophys

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2-carboxylic acids [3] and corresponding esters [4]. Pyrrole-2-carboxylates are also useful substrates for the preparation of more complex pyrrole containing systems [5] such as ketorolac, a drug with anti-inflammatory and analgesic properties [6]. It is noted that the 2-acylpyrrole motif is widespread in nature. There are many examples of 2-acylpyrrole based molecules (Figure 1) with various biological activities [7,8]. Representative examples are pyoluteorin and pyrrolomycin D, secondary metabolites produced by marine Conformational Preferences of 2-Acylpyrroles in Light of FT-IR and DFT StudiesAlina T Dubis* Institute of Chemistry, University of Białystok, Hurtowa 1, Poland AbstractConformations of alpha-substituted pyrroles have been effectively studied using spectroscopic methods assisted by theoretical calculations developed in the recent decade. The question of how to effectively study the conformation of 2-acylpyrrole no longer remains unanswered. The detailed spectroscopic studies conducted in the last decade and interpreted on the basis of theoretical calculations provide a satisfactory answer to that question. Based on the Density Functional Theory (DFT) calculations of conformational properties of 2-acylpyrroles, for which two stable rotameric forms were predicted, syn and anti-conformers have been studied either by experimental or theoretical methods. The family of 2-acylpyrroles have both a proton donor N-H group and a proton acceptor C=O group. This structure favors the formation of doubly hydrogen-bonded cyclic dimers connected by two N-H...O=C bonds. The tendency to form cyclic dimers stabilizes the syn-conformation. Due to these properties 2-acylpyrroles can be used as structural models for the conformational analysis of peptides.This review summarizes recent investigations of conformations of 2-acylpyrroles, with a particular emphasis on the hydrogen bonds forming within these systems. The influence of 2-substitution on different aspects of stability of these molecular systems and the usefulness of infrared spectroscopy supported by theoretical calculations in H-bonds and conformational studies are discussed. Among the molecular properties hydrogen bond energy, structural characteristics such as C=O bond length of dimers and unique spectral features of 2-acylpyrroles that can be used to predict and investigate the conformation and structure of proteins are considered.Graphical abstract. The potential energy diagram of 2-acylpyrroles as a function of the dihedral angle pyrrole ringcarbonyl group of bond rotation. Most stable conformer syn converts to conformer anti via the transition state TS1; less stable conformer anti converts to conformer syn via the transition state TS2. conformational research and can greatly support experimental work with quite good accuracy. Among the most useful parameters are geometrical parameters, relative conformational energies, barriers to internal rotation and vibrational frequencies for each conformer. Journal of Physical Chemistry & BiophysicsEnergy differ...

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Section: Introductionmentioning

confidence: 99%

Conformational Preferences of 2-Acylpyrroles in Light of FT-IR and DFT Studies

Dubis

2014

J Phys Chem Biophys

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“…Pyrrole and its derivatives are of great importance in organic and biochemistry and have found many applications in medicine and technology [81,82]. Many pyrrole derivatives have shown interesting biological properties [83][84][85][86][87], pharmaceutical importance, [88,89], and use as monomers for conducting polymers and nonlinear optics material [90].…”

Section: Pyrrolesmentioning

confidence: 99%

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

Beagle

2015

Topics in Heterocyclic Chemistry

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Application of benzotriazole methodology for the preparation of nitrogen-containing heterocyclic compounds is summarized in this review. The characteristic advantages of benzotriazole are first briefly considered followed by an overview of its use in the synthesis of heterocycles organized by the ring size. Finally, the use of benzotriazole in the synthesis of bicyclic systems is showcased in only selected examples.

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“…In this context,t here is much current interestint he development of syntheses of pyrroles by multiple bond-forming strategies, especially by application of multicomponent reactions(MCRs). [22] Among the classical named methodsf or pyrrole synthesis, the Hantzsch reaction is surprisingly underdeveloped. Hantzsch's1 890 originaln ote [23] described as ingle pyrrole derivativea nd the authors of ap aper published in 1970 stated that they had been able to locate only eight additional examples published in the intervening 80-year period,w iths tructural variation limited to alkyl substituents at C-4 and C-5 and yields under 45 %.…”

Section: Introductionmentioning

confidence: 99%

Three‐Component Synthesis of Pyrrole‐Related Nitrogen Heterocycles by a Hantzsch‐Type Process: Comparison between Conventional and High‐Speed Vibration Milling Conditions

et al. 2016

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The use of solvent-free, high-speed vibration milling conditions has allowed the development of ao ne-pot telescoped process for the synthesis of pyrroles starting from ketones, primary amines, and b-dicarbonyl compounds and comprising an initial a-iodination followed by an in situ three-component Hantzsch-type reaction. This methodw as compared with as olution-based protocol from a-iodoketones, primary amines,a nd b-dicarbonyl compounds. Although both protocols were far more general than previous Hantzsch-type pyrrole syntheses, the mechanochemical methodw as superior in that it afforded considerably higher yields in spite of comprising an additional step. The stereochemicali ntegrity of the pyrroles obtained from chiral aaminoesters wasm aintained. This solvent-free method was also used for the efficient preparationo fter-a nd quater-aryl/ heteroaryl frameworks containing two pyrrole units and avariety of fused pyrrole systems, including benzo[g]indoles, indeno[1,2-b]pyrroles, indoles,and homoindoles.

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Recent advances in the synthesis of pyrroles by multicomponent reactions

Cited by 662 publications

References 109 publications

Conformational Preferences of 2-Acylpyrroles in Light of FT-IR and DFT Studies

Conformational Preferences of 2-Acylpyrroles in Light of FT-IR and DFT Studies

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

Three‐Component Synthesis of Pyrrole‐Related Nitrogen Heterocycles by a Hantzsch‐Type Process: Comparison between Conventional and High‐Speed Vibration Milling Conditions

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