7228-38-8Relevant articles and documents
Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes
Rogers, David A.,Gallegos, Jillian M.,Hopkins, Megan D.,Lignieres, Austin A.,Pitzel, Amy K.,Lamar, Angus A.
, (2019/08/12)
A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use with NCS. According to mechanistic studies described within, the reaction is speculated to proceed via a single electron oxidation of NCS utilizing methylene green under visible-light photoredox pathway. The photo-oxidation of NCS amplifies the electrophilicity of the chlorine atom of the NCS, thus leading to enhanced reactivity as a chlorinating reagent with aromatic substrates.
Synthesis of important intermediate of berberine
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Paragraph 0017; 0020; 0021; 0022; 0023; 0024, (2018/07/30)
The invention discloses synthesis of an important intermediate of berberine. A synthesis method comprises the following steps: reacting 1,3-benzodioxole with chlorine in an organic solvent to produce5-chloro-1,3-benzodioxole; reacting 5-chloro-1,3-benzodioxole with a magnesium rod in an ether solvent to produce a Grignard reagent; reacting 2,3-dimethoxybenzoic acid with aziridine in an organic solvent under the action of a dehydrating agent to produce 1-aziridine-2,3-dimethoxyphenylethanone; and under the action of the Grignard reagent, subjecting 1-aziridine-2,3-dimethoxyphenylethanone to ring opening so as to obtain the important intermediate of berberine, i.e., N-(2-(benzo[d][1,3]dioxin-5-yl)ethyl)-2,3-dimethoxybenzamide. The synthesis method is mild in reaction conditions and simple to operate.
Practical and metal-free electrophilic aromatic halogenation by interhalogen compounds generated in situ from N-halosuccinimide and catalytic TMSCL
Maibunkaew, Tapanee,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Bunrit, Anon,Ruchirawat, Somsak
supporting information, p. 1769 - 1775 (2014/08/05)
Halomonochloride compounds (ClCl, BrCl, ICl) generated in situ from N-halosuccinimide and catalytic chlorotrimethylsilane (TMSCl, 0.1 equiv) can efficiently halogenate aromatic compounds to give halogenated products in good to excellent yields and selectivities. The reaction can be carried out at room temperature or at lower temperatures, requires only one hour, is practical to apply to a wide range of substrates, and provides a simple access to a variety of haloarene compounds. Georg Thieme Verlag Stuttgart New York.