Regioselective addition of Grignard reagents to N -acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ 5 -2-oxopiperazines.

Autor: St Hilaire VR; Biomanufacturing Research Institute and Technology Enterprise (BRITE), North Carolina Central University, Durham, North Carolina 27707, United States., Hopkins WE; Biomanufacturing Research Institute and Technology Enterprise (BRITE), North Carolina Central University, Durham, North Carolina 27707, United States., Miller YS; Biomanufacturing Research Institute and Technology Enterprise (BRITE), North Carolina Central University, Durham, North Carolina 27707, United States., Dandepally SR; Biomanufacturing Research Institute and Technology Enterprise (BRITE), North Carolina Central University, Durham, North Carolina 27707, United States., Williams AL; Biomanufacturing Research Institute and Technology Enterprise (BRITE), North Carolina Central University, Durham, North Carolina 27707, United States.; Department of Pharmaceutical Sciences, North Carolina Central University, Durham, North Carolina 27707, United States.
Jazyk: angličtina
Zdroj: Beilstein journal of organic chemistry [Beilstein J Org Chem] 2019 Jan 08; Vol. 15, pp. 72-78. Date of Electronic Publication: 2019 Jan 08 (Print Publication: 2019).
DOI: 10.3762/bjoc.15.8
Abstrakt: The regioselective addition of Grignard reagents to mono- and disubstituted N -acylpyrazinium salts affording substituted 1,2-dihydropyrazines in modest to excellent yields (45-100%) is described. Under acidic conditions, these 1,2-dihydropyrazines can be converted to substituted Δ 5 -2-oxopiperazines providing a simple and efficient approach towards their preparation.
Databáze: MEDLINE