Supramolecular structure of 5-methyl-5-phenyl hydantoin and hydrogen-bonding patterns in 5,5′-substituted hydantoins

Delgado, Gerzon E.; Rodríguez, Jesús; Mora, Asiloé J.; Bruno-Colmenárez, Julia; Uzcátegui, Jorge; Chacón, Cecília

doi:10.1080/15421406.2015.1107745

Cited by 10 publications

(7 citation statements)

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“…Because of aqueous reaction conditions, there is no need for dry solvents. Most commonly, a mixture of water with ethanol (or methanol) or methanol itself is employed [ 138 , 139 , 140 , 141 , 142 , 143 , 144 , 145 , 146 , 147 , 148 , 149 , 150 , 151 , 152 , 153 , 154 , 155 , 156 , 157 , 158 , 159 , 160 , 161 , 162 , 163 , 164 , 165 , 166 , 167 , 168 , 169 , 170 , 171 , 172 , 173 , 174 , 175 , 176 , 177 , 178 , 179 , 180 , 181 , 182 , 183 , 184 , 185 , 186 , 187 , 188 ...…”

Section: Experimental Conditionsmentioning

confidence: 99%

The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity

et al. 2021

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Hydantoins and their hybrids with other molecules represent a very important group of heterocycles because they exhibit diverse biological and pharmacological activities in medicinal and agrochemical applications. They also serve as key precursors in the chemical or enzymatic synthesis of significant nonnatural α-amino acids and their conjugates with medical potential. This review provides a comprehensive treatment of the synthesis of hydantoins via the Bucherer–Bergs reaction including the Hoyer modification but limited to free carbonyl compounds or carbonyl compounds protected as acetals (ketals) and cyanohydrins used as starting reaction components. In this respect, the Bucherer–Bergs reaction provides an efficient and simple method in the synthesis of important natural products as well as for the preparation of new organic compounds applicable as potential therapeutics. The scope and limitations, as well as a comparison with some other methods for preparing hydantoins, are also discussed.

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Section: Experimental Conditionsmentioning

confidence: 99%

The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity

et al. 2021

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“…With the interested in the structural characterization of compounds with possible pharmacological activity (Vizcaya et al, 2012;Gonzalez et al, 2012;Delgado et al, 2015;Delgado et al, 2016;Delgado et al, 2018a;2018b), the present work is focused on report the X-ray powder diffraction data for the new heterocyclic chalcone (E)-3-(5-bromo thiophen-2yl)-1-(2,5-dichlorothiophen-3-yl)-2-propen-1-one, which was prepared among a series of thiophene derivative chalcones as potential anti-cancer and anti-microbial agents (Al-Maqtari et al, 2015). Its crystal structure was recently reported and crystallizes in the monoclinic space group P2 1 /n (Delgado et al, 2018b).…”

Section: Introductionmentioning

confidence: 99%

X-Ray Powder Diffraction Data for a New Thiophene Chalcone Obtained by a Claisen-Schmidt Reaction

Delgado¹,

Delgado-Niño²,

Jamalis³

2019

PTQ

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Chalcones and their heterocyclic derivatives have gained considerable importance in recent years due to their wide range of pharmacological properties including anti-AIDS agents, anti-bacterial, anti-malarial, antiinflammatory, anti-leishmanial, anti-oxidant, anti-cancer, anti-tuberculosis anti-microbial activity. These important compounds are conventionally synthesized by Claisen-Schmidt condensation reaction in which aldehyde reacted with acetophenone in the presence of aqueous alkaline bases. Hence the importance of characterizing new derivatives using different techniques both spectroscopic and diffractometric to know their molecular and crystalline structure, but also techniques that allow to study their biological properties to know their possible applications. X-ray powder diffraction is the technique most widely used for the identification of crystalline materials and hence the importance of reporting powder patterns in the Powder Diffraction File database. Therefore, the objective of this investigation is to obtain and reported good quality X-ray powder diffraction data (d-spacing and relative intensity of observed hkl reflections) of the new hetererocyclic chalcone derivative; (E)-3-(5-bromo thiophen-2-yl)-1-(2,5-dichlorothiophen-3-yl)-2-propen-1-one. This new compound was synthesized by Claisen-Schmidt condensation method among a series of thiophene derivative chalcones as potential anti-cancer and anti-microbial agents. The powder pattern was indexed in the monoclinic space group P21/n with unit cell parameters a= 4.0323(7) Å, b= 13.551(3) Å, c= 23.511(5) Å, β= 94.27(1), Z = 4, V= 1281.1(3) Å3, and figures of merit M20= 18.2 and F30= 47.6 (0.0143, 44). All measured lines were indexed and are consistent with the monoclinic space group.

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“…As part of our research work to explore the synthesis and structural characterization of hydantoin and thiohydantoin derivative compounds (Delgado et al, 2007;2012;2013;2015a;2015b;2015c;2016;Sulbaran et al, 2007;Uzcátegui et al, 2009;Seijas et al, 2010;, we have investigated the synthesis, crystalline and molecular structure of rac-2thiohydantoin-valine, systematic name rac-5isopropyl-2-tioxoimidazolidin-4-one, synthesized from a solvent-free reaction.…”

Section: Introductionmentioning

confidence: 99%

SOLVENT-FREE SYNTHESIS AND CRYSTAL STRUCTURE OF rac-2-THIOHYDANTOIN-VALINE

Delgado¹,

Mora²,

González³

et al. 2019

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Thiohydantoins have been used in the manufacture of medicines and in industrial processes. Depending on the nature and type of substitution on the heterocyclic ring, these compounds may display pharmaceutical and biological activity with a variety of applications as antiepileptic, antitumoral, antiinflammatory, and principally for the treatment of prostate cancer. In this study, a new thiohydantoin was synthetized from the valine amino acid and structurally characterized. The title compound, C6H10N2O2S, with systematic name rac-5-isopropyl-2-tioxoimidazolidin-4-one, has been synthetized by a solvent-free synthesis. The heterocyclic compound was characterized by spectroscopic infrared (FTIR) and nuclear magnetic resonance (NMR) techniques, powder and single-crystal X-ray diffraction analysis (XRD). This material crystallizes in the monoclinic space group P21/c. In the supramolecular structure, the molecules are joined by N- --H···O and N---H···S hydrogen bonds, forming centrosymmetric R2 2(8) dimers and C2 2(9) chains that run along the [001] direction in an infinite one-dimensional network.

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Supramolecular structure of 5-methyl-5-phenyl hydantoin and hydrogen-bonding patterns in 5,5′-substituted hydantoins

Cited by 10 publications

References 46 publications

The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity

The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity

X-Ray Powder Diffraction Data for a New Thiophene Chalcone Obtained by a Claisen-Schmidt Reaction

SOLVENT-FREE SYNTHESIS AND CRYSTAL STRUCTURE OF rac-2-THIOHYDANTOIN-VALINE

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