Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems
3-(Vinyl-/buta-1,3-dien-1-yl/4-phenylbuta-1,3-dien-1-yl)-4-chloro quinolines and quinolin-4(1H)-ones were synthesized by ultrasound-assisted Wittig reaction of the corresponding 4-chloro-3-formylquinoline and 3-formylquinolin-4(1H)-ones with nonstabilized ylides. Ease execution, mild conditions, and...
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| Format: | Article |
| Language: | English |
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Wiley
2022-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2022/4807767 |
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| author | Wahiba Frites Massaab Khalfaoui Lamouri Hammal Vera L. M. Silva Artur M. S. Silva |
| author_facet | Wahiba Frites Massaab Khalfaoui Lamouri Hammal Vera L. M. Silva Artur M. S. Silva |
| author_sort | Wahiba Frites |
| collection | DOAJ |
| description | 3-(Vinyl-/buta-1,3-dien-1-yl/4-phenylbuta-1,3-dien-1-yl)-4-chloro quinolines and quinolin-4(1H)-ones were synthesized by ultrasound-assisted Wittig reaction of the corresponding 4-chloro-3-formylquinoline and 3-formylquinolin-4(1H)-ones with nonstabilized ylides. Ease execution, mild conditions, and high yields make this method exploitable for the generation of libraries of 3-substituted 4-chloroquinolines and quinolin-4(1H)-ones with extended π-conjugated systems. To demonstrate the usefulness of these compounds as precursors for the synthesis of more complex structures, 3-vinylquinolin-4(1H)-ones were used as dienes in the Diels–Alder reaction with N-methylmaleimide to produce novel acridone derivatives. The attempted Diels–Alder reaction with 3-(buta-1,3-dien-1-yl)quinolin-4(1H)-one did not afford the expected cycloadduct; instead, 2-methyl-2H-pyrano[3,2-c]quinoline was obtained. The structures and stereochemistry of the new compounds were established by NMR studies. |
| format | Article |
| id | doaj-art-40ae0a6ea7d04207bc21336389e5cdb9 |
| institution | Kabale University |
| issn | 2090-9071 |
| language | English |
| publishDate | 2022-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-40ae0a6ea7d04207bc21336389e5cdb92025-02-03T05:57:26ZengWileyJournal of Chemistry2090-90712022-01-01202210.1155/2022/4807767Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated SystemsWahiba Frites0Massaab Khalfaoui1Lamouri Hammal2Vera L. M. Silva3Artur M. S. Silva4Laboratory of Applied Organic Chemistry (LCOA)Laboratory of Applied Organic Chemistry (LCOA)Laboratory of Applied Organic Chemistry (LCOA)LAQV-REQUIMTELAQV-REQUIMTE3-(Vinyl-/buta-1,3-dien-1-yl/4-phenylbuta-1,3-dien-1-yl)-4-chloro quinolines and quinolin-4(1H)-ones were synthesized by ultrasound-assisted Wittig reaction of the corresponding 4-chloro-3-formylquinoline and 3-formylquinolin-4(1H)-ones with nonstabilized ylides. Ease execution, mild conditions, and high yields make this method exploitable for the generation of libraries of 3-substituted 4-chloroquinolines and quinolin-4(1H)-ones with extended π-conjugated systems. To demonstrate the usefulness of these compounds as precursors for the synthesis of more complex structures, 3-vinylquinolin-4(1H)-ones were used as dienes in the Diels–Alder reaction with N-methylmaleimide to produce novel acridone derivatives. The attempted Diels–Alder reaction with 3-(buta-1,3-dien-1-yl)quinolin-4(1H)-one did not afford the expected cycloadduct; instead, 2-methyl-2H-pyrano[3,2-c]quinoline was obtained. The structures and stereochemistry of the new compounds were established by NMR studies.http://dx.doi.org/10.1155/2022/4807767 |
| spellingShingle | Wahiba Frites Massaab Khalfaoui Lamouri Hammal Vera L. M. Silva Artur M. S. Silva Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems Journal of Chemistry |
| title | Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems |
| title_full | Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems |
| title_fullStr | Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems |
| title_full_unstemmed | Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems |
| title_short | Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems |
| title_sort | ultrasound assisted wittig reaction for the synthesis of 3 substituted 4 chloroquinolines and quinolin 4 1h ones with extended π conjugated systems |
| url | http://dx.doi.org/10.1155/2022/4807767 |
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