Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol
Fekete, B., Palkó, M., Haukka, M., & Fülöp, F. (2017). Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol. Molecules, 22(4), Article 613. https://doi.org/10.3390/molecules22040613
© the Authors, 2017. This is an open access article distributed under the Creative Commons Attribution License.
From 2-aminonorbornene hydroxamic acids, a simple and efficient method for the preparation of pyrrolo[1,2-a]pyrimidine enantiomers is reported. The synthesis is based on domino ring-closure followed by microwave-induced retro Diels-Alder (RDA) protocols, where the chirality of the desired products is transferred from norbornene derivatives. The stereochemistry of the synthesized compounds was proven by X-ray crystallography. The absolute configuration of the product is determined by the configuration of the starting amino hydroxamic acid.
Publication in research information system
MetadataShow full item record
Except where otherwise noted, this item's license is described as © the Authors, 2017. This is an open access article distributed under the Creative Commons Attribution License.
Showing items with similar title or keywords.
N-Heterocyclic Carbene Catalyzed Quadruple Domino Reactions through α,β-Unsaturated Acyl Azolium Intermediates : Asymmetric Synthesis of Cyclopenta[c]chromenones Liu, Qiang; Chen, Xiang-Yu; Puttreddy, Rakesh; Rissanen, Kari; Enders, Dieter (Wiley, VCH Verlag GmbH & Co. KGaA, 2018)An N‐heterocyclic carbene catalyzed domino sequence via α,β‐unsaturated acyl azolium intermediates has been developed. This strategy provides a convenient enantioselective route to functionalized tricyclic coumarin derivatives ...
Retro Diels Alder protocol for regioselective synthesis of novel [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones Said, Awad I.; Palkó, Márta; Haukka, Matti; Fülöp, Ferenc (Royal Society of Chemistry, 2020)Reactions of diastereochemically varied norbornene-condensed 2-thioxopyrimidin-4-ones6and10with variously functionalized hydrazonoyl chlorides2a-hgave regioselectively angular norbornene-based [1,2,4]triazolo[4,3-a]pyrim ...
Extending the Series: Synthesis and Characterization of a Dicationic N-Heterocyclic Selenium Carbene Analogue Dutton, Jason; Tuononen, Heikki; Jennings, Michael; Ragogna, Paul (ACS, 2006)The room-temperature reaction between the Dipp2DAB ligand, SnCl2, and SeCl4 results in the quantitative formation of a dicationic N-heterocyclic “carbenoid”. This represents the first example of a chalcogenium dication ...
N-Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Pentacyclic Spirooxindoles via [3+3] Annulations of Isatin-Derived Enals and Cyclic N-Sulfonyl Ketimines Liu, Qiang; Chen, Xiangyu; Li, Sun; Rissanen, Kari; Enders, Dieter (Wiley - VCH Verlag GmbH & Co. KGaA, 2019)A convenient enantioselective route to new types of pentacyclic spirooxindoles via [3+3] annulation reactions of isatin-derived enals and cyclic N-sulfonyl ketimines, using N-heterocyclic carbene (NHC) catalysis has ...
Organocatalytic Oxa-Michael/Michael/Michael/Aldol Condensation Quadruple Domino Sequence : Asymmetric Synthesis of Tricyclic Chromanes Kumar, Mukesh; Chauhan, Pankaj; Bailey, Stephen J.; Jafari, Ehsan; von Essen, Carolina; Rissanen, Kari; Enders, Dieter (American Chemical Society, 2018)An efficient and highly stereoselective one-pot, four-component synthesis of functionalized tricyclic chromanes has been achieved through an organocatalyzed quadruple domino reaction. The reaction sequence involves an ...