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Gräßle S, Vanderheiden S, Hodapp P, et al. Solid Phase Synthesis of (Benzannelated) Six-Membered Heterocycles via Cyclative Cleavage of Resin-Bound Pseudo-Oxazolones. Org Lett. 2016;18(15):3598-601doi: 10.1021/acs.orglett.6b01609.
Gräßle, S., Vanderheiden, S., Hodapp, P., Bulat, B., Nieger, M., Jung, N., & Bräse, S. (2016). Solid Phase Synthesis of (Benzannelated) Six-Membered Heterocycles via Cyclative Cleavage of Resin-Bound Pseudo-Oxazolones. Organic letters, 18(15), 3598-601. https://doi.org/10.1021/acs.orglett.6b01609
Gräßle, Simone, et al. "Solid Phase Synthesis of (Benzannelated) Six-Membered Heterocycles via Cyclative Cleavage of Resin-Bound Pseudo-Oxazolones." Organic letters vol. 18,15 (2016): 3598-601. doi: https://doi.org/10.1021/acs.orglett.6b01609
Gräßle S, Vanderheiden S, Hodapp P, Bulat B, Nieger M, Jung N, Bräse S. Solid Phase Synthesis of (Benzannelated) Six-Membered Heterocycles via Cyclative Cleavage of Resin-Bound Pseudo-Oxazolones. Org Lett. 2016 Aug 05;18(15):3598-601. doi: 10.1021/acs.orglett.6b01609. Epub 2016 Jul 11. PMID: 27399339.
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Org Lett. 2016 Aug 05;18(15):3598-601. doi: 10.1021/acs.orglett.6b01609. Epub 2016 Jul 11.

Solid Phase Synthesis of (Benzannelated) Six-Membered Heterocycles via Cyclative Cleavage of Resin-Bound Pseudo-Oxazolones.

Organic letters

Simone Gräßle, Sylvia Vanderheiden, Patrick Hodapp, Bekir Bulat, Martin Nieger, Nicole Jung, Stefan Bräse

Affiliations

  1. Institute of Toxicology and Genetics, Karlsruhe Institute of Technology , Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.
  2. Institute of Organic Chemistry, Karlsruhe Institute of Technology , Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
  3. Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki , P.O Box 55, A. I. Virtasen aukio 1, 00014 Helsinki, Finland.

PMID: 27399339 DOI: 10.1021/acs.orglett.6b01609

Abstract

A solid supported procedure for the synthesis of benzoxazinones, dihydropyrazinones, quinoxalinones, and dihydrooxazinones using immobilized oxazolones in combination with difunctional nucleophiles as cleavage agent is presented. The scope of the novel method has been demonstrated through subsequent modification of the parent oxazolone scaffold on solid supports using conversions with electrophiles or CuAAC reactions to give functionalized pyrazin-2-ones. The described method allows the synthesis of the target heterocycles in good yields via three to five steps on solid phases with only one chromatographic purification step.

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