- Iterative addition of carbon nucleophiles toN,N-dialkyl carboxamides for synthesis of α-tertiary amines
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A protocol for the synthesis of α-tertiary amines was developed by iterative addition of carbon nucleophiles toN,N-dialkyl carboxamides. Nucleophilic 1,2-addition of organolithium reagents to carboxamides forms anionic tetrahedral carbinolamine (hemiaminal) intermediates, which are subsequently treated with bromotrimethylsilane (Me3SiBr) followed by organomagnesium (Grignard) reagents, organolithium reagents or tetrabutylammonium cyanide, affording α-tertiary amines. Employment of (trimethylsilyl)methylmagnesium bromide as the 2ndnucleophile allowed for aza-Peterson olefination of the resulting α-tertiary (trimethylsilyl)methylamines with acidic work-up, resulting in the formation of 1,1-diarylethylenes.
- Chen, Jiahua,Chiba, Shunsuke,Lim, Jun Wei,Ong, Derek Yiren
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- Solvent-promoted highly selective dehydrogenation of tetrahydroisoquinolines without catalyst and hydrogen acceptor
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An unusual solvent DMF-promoted dehydrogenation of 1-substituted 1,2,3,4-tetrahydroisoquinolines to synthesize cyclic imines is described. This environmentally friendly reaction features no requirement of any metal catalysts, oxidants, or hydrogen acceptors. A wide range of structurally varied 3,4-dihydroisoquinolines can be obtained with good yields and excellent chemoselectivities.
- Feng, Guang-Shou,Ji, Yue,Liu, Hui-Fang,Shi, Lei,Zhou, Yong-Gui
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supporting information
p. 747 - 749
(2016/02/05)
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- Studies on cerebral protective agents. IX. Synthesis of novel 1,2,3,4-tetrahydroisoquinolines as N-methyl-D-aspartate antagonists
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A series of 1,2,3,4-tetrahydroisoquinoline derivatives were synthesized and evaluated for anticonvulsant activity against intracerebro-ventriculas (i.c.v.) N-methyl-D-aspartate (NMDA)-induced seizures in mice. Among these compounds, (+)-1-methyl-1-phenyl-
- Ohkubo, Mitsuru,Kuno, Atsushi,Katsuta, Kiyotaka,Ueda, Yoshiko,Shirakawa, Kiyoharu,Nakanishi, Hajime,Nakanishi, Isao,Kinoshita, Takayoshi,Takasugi, Hisashi
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- Bicyclic amine compound and a process for the preparation thereof
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The invention relates to a compound useful as an anticonvulsant, and for treatment of delayed neuronal death, the compound being a bicyclic amine of the formula: STR1 wherein R1 is lower alkyl, R2 is aryl which may have one or more s
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