Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile
An efficient method for the synthesis of pharmaceutically and high-tech prospective 2-(3-amino-2,4-dicyanophenyl)pyrroles (in up to 88% yield) via the reaction of easily available substituted acylethynylpyrroles with malononitrile has been developed. The reaction proceeds in the KOH/MeCN system at 0...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/23/8528 |
| _version_ | 1827642851251453952 |
|---|---|
| author | Maxim D. Gotsko Ivan V. Saliy Igor A. Ushakov Lyubov N. Sobenina Boris A. Trofimov |
| author_facet | Maxim D. Gotsko Ivan V. Saliy Igor A. Ushakov Lyubov N. Sobenina Boris A. Trofimov |
| author_sort | Maxim D. Gotsko |
| collection | DOAJ |
| description | An efficient method for the synthesis of pharmaceutically and high-tech prospective 2-(3-amino-2,4-dicyanophenyl)pyrroles (in up to 88% yield) via the reaction of easily available substituted acylethynylpyrroles with malononitrile has been developed. The reaction proceeds in the KOH/MeCN system at 0 °C for 2 h. In the case of 2-acylethynylpyrroles without substituents in the pyrrole ring, the reaction changes direction: instead of the target 2-(3-amino-2,4-dicyanophenyl)pyrroles, the unexpected formation of pyrrolyldienols and products of their intramolecular cyclization, 3-amino-1-acylethylidene-2-cyanopyrrolizines, is observed. |
| first_indexed | 2024-03-09T17:38:44Z |
| format | Article |
| id | doaj.art-7483ba14ebaf4e2ebff47a3bb1b943d4 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T17:38:44Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7483ba14ebaf4e2ebff47a3bb1b943d42023-11-24T11:43:44ZengMDPI AGMolecules1420-30492022-12-012723852810.3390/molecules27238528Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with MalononitrileMaxim D. Gotsko0Ivan V. Saliy1Igor A. Ushakov2Lyubov N. Sobenina3Boris A. Trofimov4A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaAn efficient method for the synthesis of pharmaceutically and high-tech prospective 2-(3-amino-2,4-dicyanophenyl)pyrroles (in up to 88% yield) via the reaction of easily available substituted acylethynylpyrroles with malononitrile has been developed. The reaction proceeds in the KOH/MeCN system at 0 °C for 2 h. In the case of 2-acylethynylpyrroles without substituents in the pyrrole ring, the reaction changes direction: instead of the target 2-(3-amino-2,4-dicyanophenyl)pyrroles, the unexpected formation of pyrrolyldienols and products of their intramolecular cyclization, 3-amino-1-acylethylidene-2-cyanopyrrolizines, is observed.https://www.mdpi.com/1420-3049/27/23/8528acylethynylpyrrolesmalononitrile2-(3-amino-2,4-dicyanophenyl)pyrrolespyrrolyldienols3-amino-1-acylethylidene-2-cyanopyrrolizines |
| spellingShingle | Maxim D. Gotsko Ivan V. Saliy Igor A. Ushakov Lyubov N. Sobenina Boris A. Trofimov Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile Molecules acylethynylpyrroles malononitrile 2-(3-amino-2,4-dicyanophenyl)pyrroles pyrrolyldienols 3-amino-1-acylethylidene-2-cyanopyrrolizines |
| title | Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile |
| title_full | Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile |
| title_fullStr | Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile |
| title_full_unstemmed | Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile |
| title_short | Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile |
| title_sort | substituent dependent divergent synthesis of 2 3 amino 2 4 dicyanophenyl pyrroles pyrrolyldienols and 3 amino 1 acylethylidene 2 cyanopyrrolizines via reaction of acylethynylpyrroles with malononitrile |
| topic | acylethynylpyrroles malononitrile 2-(3-amino-2,4-dicyanophenyl)pyrroles pyrrolyldienols 3-amino-1-acylethylidene-2-cyanopyrrolizines |
| url | https://www.mdpi.com/1420-3049/27/23/8528 |
| work_keys_str_mv | AT maximdgotsko substituentdependentdivergentsynthesisof23amino24dicyanophenylpyrrolespyrrolyldienolsand3amino1acylethylidene2cyanopyrrolizinesviareactionofacylethynylpyrroleswithmalononitrile AT ivanvsaliy substituentdependentdivergentsynthesisof23amino24dicyanophenylpyrrolespyrrolyldienolsand3amino1acylethylidene2cyanopyrrolizinesviareactionofacylethynylpyrroleswithmalononitrile AT igoraushakov substituentdependentdivergentsynthesisof23amino24dicyanophenylpyrrolespyrrolyldienolsand3amino1acylethylidene2cyanopyrrolizinesviareactionofacylethynylpyrroleswithmalononitrile AT lyubovnsobenina substituentdependentdivergentsynthesisof23amino24dicyanophenylpyrrolespyrrolyldienolsand3amino1acylethylidene2cyanopyrrolizinesviareactionofacylethynylpyrroleswithmalononitrile AT borisatrofimov substituentdependentdivergentsynthesisof23amino24dicyanophenylpyrrolespyrrolyldienolsand3amino1acylethylidene2cyanopyrrolizinesviareactionofacylethynylpyrroleswithmalononitrile |