Stereoselective synthesis and X-ray structure determination of novel 1,2-dihydroquinolinehydrazonopropanoate derivatives
A novel series of 1,2-dihydroquinolinhydrazonopropanoate have been synthesized via a convenient aza-Michael addition reaction between hydrazinylquinolinones and ethyl propiolate in ethanol under refluxing temperature. The structures for all obtained products were confirmed with FTIR, NMR spectrums,...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-02-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844024012799 |
| _version_ | 1797267843112239104 |
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| author | Hendawy N. Tawfeek Ahmed M. Tawfeek Stefan Bräse Martin Nieger Essmat M. El-Sheref |
| author_facet | Hendawy N. Tawfeek Ahmed M. Tawfeek Stefan Bräse Martin Nieger Essmat M. El-Sheref |
| author_sort | Hendawy N. Tawfeek |
| collection | DOAJ |
| description | A novel series of 1,2-dihydroquinolinhydrazonopropanoate have been synthesized via a convenient aza-Michael addition reaction between hydrazinylquinolinones and ethyl propiolate in ethanol under refluxing temperature. The structures for all obtained products were confirmed with FTIR, NMR spectrums, as well as mass spectrometry. In addition, the monoclinic structure for compounds 8a, 8c, and 8d was also confirmed via X-ray crystallography analyses. The E-configuration for the obtained products was confirmed form the X-ray analysis. On the other hand, the crystal packing shows that the intermolecular and hydrogen bonds between atoms are parallel to the bc plan. |
| first_indexed | 2024-03-07T23:38:42Z |
| format | Article |
| id | doaj.art-cfcddc0ffea44e9c86bda78e5c847994 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-04-25T01:23:01Z |
| publishDate | 2024-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-cfcddc0ffea44e9c86bda78e5c8479942024-03-09T09:25:17ZengElsevierHeliyon2405-84402024-02-01104e25248Stereoselective synthesis and X-ray structure determination of novel 1,2-dihydroquinolinehydrazonopropanoate derivativesHendawy N. Tawfeek0Ahmed M. Tawfeek1Stefan Bräse2Martin Nieger3Essmat M. El-Sheref4Chemistry Department, Faculty of Science, Minia University, El-Minia, 61519, Egypt; Corresponding author. Chemistry Department, Faculty of Science, Minia University, El-Minia, 61519, Egypt.Chemistry Department, College of Science, King Saud University, Riyadh, 11451, Saudi ArabiaInstitute of Biological and Chemical Systems, IBCS-FMS, Karlsruhe Institute of Technology, 76131, Karlsruhe, Germany; Corresponding author. Institute of Biological and Chemical Systems, IBCS-FMS, Karlsruhe Institute of Technology, 76131 Karlsruhe, Germany.Department of Chemistry, University of Helsinki, PO Box 55, A. I. Virtasen Aukio 1, 00014, Helsinki, FinlandChemistry Department, Faculty of Science, Minia University, El-Minia, 61519, EgyptA novel series of 1,2-dihydroquinolinhydrazonopropanoate have been synthesized via a convenient aza-Michael addition reaction between hydrazinylquinolinones and ethyl propiolate in ethanol under refluxing temperature. The structures for all obtained products were confirmed with FTIR, NMR spectrums, as well as mass spectrometry. In addition, the monoclinic structure for compounds 8a, 8c, and 8d was also confirmed via X-ray crystallography analyses. The E-configuration for the obtained products was confirmed form the X-ray analysis. On the other hand, the crystal packing shows that the intermolecular and hydrogen bonds between atoms are parallel to the bc plan.http://www.sciencedirect.com/science/article/pii/S2405844024012799Aza-michael additionHydrazono-hydrazidesStereoselective synthesis4-Hydrazinyl-quinolin-2(1H)-OnesEthyl propiolate1,2-Dihydroquinolin-4-yl(hydrazono)propanoate and X-ray crystallography |
| spellingShingle | Hendawy N. Tawfeek Ahmed M. Tawfeek Stefan Bräse Martin Nieger Essmat M. El-Sheref Stereoselective synthesis and X-ray structure determination of novel 1,2-dihydroquinolinehydrazonopropanoate derivatives Heliyon Aza-michael addition Hydrazono-hydrazides Stereoselective synthesis 4-Hydrazinyl-quinolin-2(1H)-Ones Ethyl propiolate 1,2-Dihydroquinolin-4-yl(hydrazono)propanoate and X-ray crystallography |
| title | Stereoselective synthesis and X-ray structure determination of novel 1,2-dihydroquinolinehydrazonopropanoate derivatives |
| title_full | Stereoselective synthesis and X-ray structure determination of novel 1,2-dihydroquinolinehydrazonopropanoate derivatives |
| title_fullStr | Stereoselective synthesis and X-ray structure determination of novel 1,2-dihydroquinolinehydrazonopropanoate derivatives |
| title_full_unstemmed | Stereoselective synthesis and X-ray structure determination of novel 1,2-dihydroquinolinehydrazonopropanoate derivatives |
| title_short | Stereoselective synthesis and X-ray structure determination of novel 1,2-dihydroquinolinehydrazonopropanoate derivatives |
| title_sort | stereoselective synthesis and x ray structure determination of novel 1 2 dihydroquinolinehydrazonopropanoate derivatives |
| topic | Aza-michael addition Hydrazono-hydrazides Stereoselective synthesis 4-Hydrazinyl-quinolin-2(1H)-Ones Ethyl propiolate 1,2-Dihydroquinolin-4-yl(hydrazono)propanoate and X-ray crystallography |
| url | http://www.sciencedirect.com/science/article/pii/S2405844024012799 |
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