A novel synthesis of 2-oxazolines from diketene by using DAST via Beckmann rearrangement as been described. The route involves a one-pot amidation of diketene with different amines at 70°C in the presence of toluene to form corresponding amides followed by reacting the amides with K2CO3 and DMF at room temperature to form corresponding carboxamides and carboxylates. The carboxamides and carboxylates are then reacted with NH2OH•HCL and NaOAc in presence of ethanol and water to form Ketoximes which are then reacted in one pot synthesis with DAST and dichloromethane at room temperature to form corresponding oxazolines via Beckmann rearrangement. Ketoximes are one of the most popular functional groups and are readily prepared by a number of methods. The initial step of our study was the strategic formation of the ketoxime from carboxamides species which would then be converted to corresponding oxazolines via Beckmann rearrangement. Each new compound has been elucidated through 1H-NMR and 13C-NMR. The Characterization data of compound was also agrees with the molecular masses of HRMS (ESI-TOF). Indeed, all the corresponding products were obtained with a good yield. The studies utilizing this strategy for the production of oxazolines are ongoing in our laboratory. Further expansion of the substrate scope, elucidating the mechanism and exploring the applications of this transformation are now under investigation in our laboratory. We are hopeful; the synthesis of 2-oxazolines from diketene by using DAST via Beckmann rearrangement will be useful in many scientific researches.
| Published in | Modern Chemistry (Volume 10, Issue 2) |
| DOI | 10.11648/j.mc.20221002.14 |
| Page(s) | 56-67 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2022. Published by Science Publishing Group |
2-Oxazoline, DAST, Beckmann Rearrangement
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APA Style
Tony Wheellyam Pouambeka, Guy Crepin Enoua, Narcisse Nicaise Obaya, Bob Wilfrid Loumouamou, Hubert Makomo, et al. (2022). Synthesis of 2-Oxazolines from Diketene Using DAST via Beckmann Rearrangement. Modern Chemistry, 10(2), 56-67. https://doi.org/10.11648/j.mc.20221002.14
ACS Style
Tony Wheellyam Pouambeka; Guy Crepin Enoua; Narcisse Nicaise Obaya; Bob Wilfrid Loumouamou; Hubert Makomo, et al. Synthesis of 2-Oxazolines from Diketene Using DAST via Beckmann Rearrangement. Mod. Chem. 2022, 10(2), 56-67. doi: 10.11648/j.mc.20221002.14
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Download@article{10.11648/j.mc.20221002.14,
author = {Tony Wheellyam Pouambeka and Guy Crepin Enoua and Narcisse Nicaise Obaya and Bob Wilfrid Loumouamou and Hubert Makomo and Victor N’Goka},
title = {Synthesis of 2-Oxazolines from Diketene Using DAST via Beckmann Rearrangement},
journal = {Modern Chemistry},
volume = {10},
number = {2},
pages = {56-67},
doi = {10.11648/j.mc.20221002.14},
url = {https://doi.org/10.11648/j.mc.20221002.14},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20221002.14},
abstract = {A novel synthesis of 2-oxazolines from diketene by using DAST via Beckmann rearrangement as been described. The route involves a one-pot amidation of diketene with different amines at 70°C in the presence of toluene to form corresponding amides followed by reacting the amides with K2CO3 and DMF at room temperature to form corresponding carboxamides and carboxylates. The carboxamides and carboxylates are then reacted with NH2OH•HCL and NaOAc in presence of ethanol and water to form Ketoximes which are then reacted in one pot synthesis with DAST and dichloromethane at room temperature to form corresponding oxazolines via Beckmann rearrangement. Ketoximes are one of the most popular functional groups and are readily prepared by a number of methods. The initial step of our study was the strategic formation of the ketoxime from carboxamides species which would then be converted to corresponding oxazolines via Beckmann rearrangement. Each new compound has been elucidated through 1H-NMR and 13C-NMR. The Characterization data of compound was also agrees with the molecular masses of HRMS (ESI-TOF). Indeed, all the corresponding products were obtained with a good yield. The studies utilizing this strategy for the production of oxazolines are ongoing in our laboratory. Further expansion of the substrate scope, elucidating the mechanism and exploring the applications of this transformation are now under investigation in our laboratory. We are hopeful; the synthesis of 2-oxazolines from diketene by using DAST via Beckmann rearrangement will be useful in many scientific researches.},
year = {2022}
}
TY - JOUR T1 - Synthesis of 2-Oxazolines from Diketene Using DAST via Beckmann Rearrangement AU - Tony Wheellyam Pouambeka AU - Guy Crepin Enoua AU - Narcisse Nicaise Obaya AU - Bob Wilfrid Loumouamou AU - Hubert Makomo AU - Victor N’Goka Y1 - 2022/06/27 PY - 2022 N1 - https://doi.org/10.11648/j.mc.20221002.14 DO - 10.11648/j.mc.20221002.14 T2 - Modern Chemistry JF - Modern Chemistry JO - Modern Chemistry SP - 56 EP - 67 PB - Science Publishing Group SN - 2329-180X UR - https://doi.org/10.11648/j.mc.20221002.14 AB - A novel synthesis of 2-oxazolines from diketene by using DAST via Beckmann rearrangement as been described. The route involves a one-pot amidation of diketene with different amines at 70°C in the presence of toluene to form corresponding amides followed by reacting the amides with K2CO3 and DMF at room temperature to form corresponding carboxamides and carboxylates. The carboxamides and carboxylates are then reacted with NH2OH•HCL and NaOAc in presence of ethanol and water to form Ketoximes which are then reacted in one pot synthesis with DAST and dichloromethane at room temperature to form corresponding oxazolines via Beckmann rearrangement. Ketoximes are one of the most popular functional groups and are readily prepared by a number of methods. The initial step of our study was the strategic formation of the ketoxime from carboxamides species which would then be converted to corresponding oxazolines via Beckmann rearrangement. Each new compound has been elucidated through 1H-NMR and 13C-NMR. The Characterization data of compound was also agrees with the molecular masses of HRMS (ESI-TOF). Indeed, all the corresponding products were obtained with a good yield. The studies utilizing this strategy for the production of oxazolines are ongoing in our laboratory. Further expansion of the substrate scope, elucidating the mechanism and exploring the applications of this transformation are now under investigation in our laboratory. We are hopeful; the synthesis of 2-oxazolines from diketene by using DAST via Beckmann rearrangement will be useful in many scientific researches. VL - 10 IS - 2 ER -
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