Fully Selective Synthesis of Spirocyclic-1,2-oxazine N-Oxides via Non-Catalysed Hetero Diels-Alder Reactions with the Participation of Cyanofunctionalysed Conjugated Nitroalkenes-Reference-Cited by-同舟云学术

Fully Selective Synthesis of Spirocyclic-1,2-oxazine N-Oxides via Non-Catalysed Hetero Diels-Alder Reactions with the Participation of Cyanofunctionalysed Conjugated Nitroalkenes

Published:2023-06-06 Issue:12 Volume:28 Page:4586
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Woliński Przemysław¹^ORCID,Kącka-Zych Agnieszka¹,Wróblewska Aneta²³^ORCID,Wielgus Ewelina³^ORCID,Dolot Rafał³^ORCID,Jasiński Radomir¹^ORCID

Affiliation:

1. Department of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Krakow, Poland

2. Department of Organic Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland

3. Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland

Abstract

Hetero Diels-Alder (HDA) reactions with the participation of E-2-aryl-1-cyano-1-nitroethenes and methylenecyclopentane were evaluated on the basis of experimental as well as quantumchemical data. It was found that contrary to most known HDA reactions, title processes are realised under non-catalytic conditions and with full regiocontrol. The DFT study shows, without any doubt, the polar but single-step reaction mechanism. Deeper exploration using Bonding Evolution Theory (BET) techniques gives a clear image of the sequences of electron density reorganisation along the reaction coordinate. The first C4-C5 bond is created in phase VII by merging two monosynaptic basins, while the second O1-C6 bond is created in the last phase by a donation of the nonbonding electron density of O1 to C6. Based on the research, we can conclude that the analysed reaction proceeds according to a two-stage one-step mechanism.

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Link

https://www.mdpi.com/1420-3049/28/12/4586/pdf

Reference66 articles.

1. Horsten, T., and Dehaen, W. (2021). 4,5,6,7-Tetrahydroindol-4-Ones as a Valuable Starting Point for the Synthesis of Polyheterocyclic Structures. Molecules, 26.

2. Khalid, Z., Alnuwaiser, M.A., Ahmad, H.A., Shafqat, S.S., Munawar, M.A., Kamran, K., Abbas, M.M., Kalam, M.A., and Ewida, M.A. (2022). Experimental and Computational Analysis of Newly Synthesized Benzotriazinone Sulfonamides as Alpha-Glucosidase Inhibitors. Molecules, 27.

3. Narváez-Ordoñez, E.G., Pabón-Carcelén, K.A., Zurita-Saltos, D.A., Bonilla-Valladares, P.M., Yánez-Darquea, T.G., Ramos-Guerrero, L.A., Ulic, S.E., Jios, J.J., Echeverría, G.A., and Piro, O.E. (2022). Synthesis, Experimental and Theoretical Study of Azidochromones. Molecules, 27.

4. Targeting G-quadruplex nucleic acids with heterocyclic alkaloids and their derivatives;Xiong;Eur. J. Med. Chem.,2015

5. Advancement in the development of heterocyclic nucleosides for the treatment of cancer-A review;Mirza;Nucleosides Nucleotides Nucleic Acids,2019

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