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Title
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Synthesis of functionalized pyrazin-2(1h)-ones via tele-nucleophilic substitution of hydrogen involving grignard reactants and electrophiles
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Author
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Abstract
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| 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 (SNH) in which the anionic σH adduct is quenched by electrophiles (other than a proton) before elimination takes place. Quenching the reaction with iodine (I2) or bromine (Br2) 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. |
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Language
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English
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Source (journal)
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Organic letters / American Chemical Society. - Washington, D.C.
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Publication
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Washington, D.C.
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2019
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ISSN
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1523-7060
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DOI
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10.1021/ACS.ORGLETT.9B00681
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Volume/pages
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21
:8
(2019)
, p. 2699-2703
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ISI
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000465644300044
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Pubmed ID
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30964690
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Full text (Publisher's DOI)
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Full text (open access)
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