5-(4-Chlorophenyl)-<i>N</i>,1-di-<i>o</i>-tolyl-1<i>H</i>-imidazole-2-amine
A new 2-amino imidazole derivative, 5-(4-chlorophenyl)-<i>N</i>,1-di-o-tolyl-1H-imidazole-2-amine (<b>3</b>), has been synthesized using a green approach. The reaction was conducted in a ChCl (cholinium chloride)/urea eutectic mixture, which is a nature-inspired and environme...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-05-01
|
| Series: | Molbank |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-8599/2023/2/M1648 |
| _version_ | 1797593290509385728 |
|---|---|
| author | Francesco Messa Paride Papadia Serena Perrone Antonio Salomone |
| author_facet | Francesco Messa Paride Papadia Serena Perrone Antonio Salomone |
| author_sort | Francesco Messa |
| collection | DOAJ |
| description | A new 2-amino imidazole derivative, 5-(4-chlorophenyl)-<i>N</i>,1-di-o-tolyl-1H-imidazole-2-amine (<b>3</b>), has been synthesized using a green approach. The reaction was conducted in a ChCl (cholinium chloride)/urea eutectic mixture, which is a nature-inspired and environmentally friendly reaction medium. The proposed reaction mechanism involves the preliminary regioselective alkylation of the <i>N</i><sub>sp2</sub> of guanidine (<b>2</b>), followed by an intramolecular condensation between the carbonyl moiety and the secondary <i>N′</i><sub>sp3</sub>. Finally, a tautomerization/aromatization step furnished the final product (<b>3</b>). Notably, 2-amino imidazole (<b>3</b>) could be isolated in high yield (91%), just by filtration from the DES/water mixture and subsequent crystallization; the remaining ChCl/urea could be recycled, after water removal, for four consecutive reactions without any significant drop in the (<b>3</b>) yield. The product has been fully characterized by <sup>1</sup>H, <sup>13</sup>C, 2D <sup>1</sup>H-<sup>13</sup>C HSQC, and 2D <sup>1</sup>H-<sup>13</sup>C HMBC NMR; FT-IR spectroscopy; and EI-MS spectrometry. |
| first_indexed | 2024-03-11T02:06:53Z |
| format | Article |
| id | doaj.art-0f7f57297b264f5283020520ee24de5a |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-11T02:06:53Z |
| publishDate | 2023-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-0f7f57297b264f5283020520ee24de5a2023-11-18T11:47:02ZengMDPI AGMolbank1422-85992023-05-0120232M164810.3390/M16485-(4-Chlorophenyl)-<i>N</i>,1-di-<i>o</i>-tolyl-1<i>H</i>-imidazole-2-amineFrancesco Messa0Paride Papadia1Serena Perrone2Antonio Salomone3Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali, Università del Salento, Prov.le Lecce-Monteroni, 73100 Lecce, ItalyDipartimento di Scienze e Tecnologie Biologiche ed Ambientali, Università del Salento, Prov.le Lecce-Monteroni, 73100 Lecce, ItalyDipartimento di Scienze e Tecnologie Biologiche ed Ambientali, Università del Salento, Prov.le Lecce-Monteroni, 73100 Lecce, ItalyDipartimento di Chimica, Università degli Studi di Bari “Aldo Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, 70125 Bari, ItalyA new 2-amino imidazole derivative, 5-(4-chlorophenyl)-<i>N</i>,1-di-o-tolyl-1H-imidazole-2-amine (<b>3</b>), has been synthesized using a green approach. The reaction was conducted in a ChCl (cholinium chloride)/urea eutectic mixture, which is a nature-inspired and environmentally friendly reaction medium. The proposed reaction mechanism involves the preliminary regioselective alkylation of the <i>N</i><sub>sp2</sub> of guanidine (<b>2</b>), followed by an intramolecular condensation between the carbonyl moiety and the secondary <i>N′</i><sub>sp3</sub>. Finally, a tautomerization/aromatization step furnished the final product (<b>3</b>). Notably, 2-amino imidazole (<b>3</b>) could be isolated in high yield (91%), just by filtration from the DES/water mixture and subsequent crystallization; the remaining ChCl/urea could be recycled, after water removal, for four consecutive reactions without any significant drop in the (<b>3</b>) yield. The product has been fully characterized by <sup>1</sup>H, <sup>13</sup>C, 2D <sup>1</sup>H-<sup>13</sup>C HSQC, and 2D <sup>1</sup>H-<sup>13</sup>C HMBC NMR; FT-IR spectroscopy; and EI-MS spectrometry.https://www.mdpi.com/1422-8599/2023/2/M16482-aminoimidazoleα-chloroketone<i>N</i>,<i>N′</i>-diarylguanidinedeep eutectic solventsolvent recyclesustainable synthesis |
| spellingShingle | Francesco Messa Paride Papadia Serena Perrone Antonio Salomone 5-(4-Chlorophenyl)-<i>N</i>,1-di-<i>o</i>-tolyl-1<i>H</i>-imidazole-2-amine Molbank 2-aminoimidazole α-chloroketone <i>N</i>,<i>N′</i>-diarylguanidine deep eutectic solvent solvent recycle sustainable synthesis |
| title | 5-(4-Chlorophenyl)-<i>N</i>,1-di-<i>o</i>-tolyl-1<i>H</i>-imidazole-2-amine |
| title_full | 5-(4-Chlorophenyl)-<i>N</i>,1-di-<i>o</i>-tolyl-1<i>H</i>-imidazole-2-amine |
| title_fullStr | 5-(4-Chlorophenyl)-<i>N</i>,1-di-<i>o</i>-tolyl-1<i>H</i>-imidazole-2-amine |
| title_full_unstemmed | 5-(4-Chlorophenyl)-<i>N</i>,1-di-<i>o</i>-tolyl-1<i>H</i>-imidazole-2-amine |
| title_short | 5-(4-Chlorophenyl)-<i>N</i>,1-di-<i>o</i>-tolyl-1<i>H</i>-imidazole-2-amine |
| title_sort | 5 4 chlorophenyl i n i 1 di i o i tolyl 1 i h i imidazole 2 amine |
| topic | 2-aminoimidazole α-chloroketone <i>N</i>,<i>N′</i>-diarylguanidine deep eutectic solvent solvent recycle sustainable synthesis |
| url | https://www.mdpi.com/1422-8599/2023/2/M1648 |
| work_keys_str_mv | AT francescomessa 54chlorophenylini1diioitolyl1ihiimidazole2amine AT paridepapadia 54chlorophenylini1diioitolyl1ihiimidazole2amine AT serenaperrone 54chlorophenylini1diioitolyl1ihiimidazole2amine AT antoniosalomone 54chlorophenylini1diioitolyl1ihiimidazole2amine |