Please use this identifier to cite or link to this item: http://hdl.handle.net/10995/101775
Title: Synthesis of Functionalized Pyrazin-2(1 H)-ones via Tele-Nucleophilic Substitution of Hydrogen Involving Grignard Reactants and Electrophiles
Authors: Mampuys, P.
Moseev, T. D.
Varaksin, M. V.
De Houwer, J.
Vande, Velde, C. M. L.
Chupakhin, O. N.
Charushin, V. N.
Maes, B. U. W.
Issue Date: 2019
Publisher: American Chemical Society
Citation: Synthesis of Functionalized Pyrazin-2(1 H)-ones via Tele-Nucleophilic Substitution of Hydrogen Involving Grignard Reactants and Electrophiles / P. Mampuys, T. D. Moseev, M. V. Varaksin, et al. — DOI 10.1021/acs.orglett.9b00681 // Organic Letters. — 2019. — Vol. 21. — Iss. 8. — P. 2699-2703.
Abstract: The reaction of 6-chloro-1-methylpyrazin-2(1H)-one with Grignard reactants followed by quenching with different electrophiles gave access to a variety of 3,6-difunctionalized 1-methylpyrazin-2(1H)-ones. This regioselective three-component reaction represents the first example of a tele-nucleophilic substitution of hydrogen (S N H ) in which the anionic σ H adduct is quenched by electrophiles (other than a proton) before elimination takes place. Quenching the reaction with iodine (I 2 ) or bromine (Br 2 ) provides an alternative reaction pathway, yielding a 3-functionalized 6-chloro-1-methylpyrazin-2(1H)-one or 5-bromo-6-chloro-1-methylpyrazin-2(1H)-one, respectively. The halogens present offer opportunities for further selective transformations. Copyright © 2019 American Chemical Society.
URI: http://hdl.handle.net/10995/101775
Access: info:eu-repo/semantics/openAccess
SCOPUS ID: 85064718096
PURE ID: 9312779
b396e911-a005-46a8-8205-69d1fb275e2e
ISSN: 15237060
DOI: 10.1021/acs.orglett.9b00681
Appears in Collections:Научные публикации, проиндексированные в SCOPUS и WoS CC

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