- A simple method of synthesis of (±)-2,3-diarylpiperazines and a novel method of resolution of (±)-2,3-diphenylpiperazine
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Intramolecular reductive coupling of diimines in the presence of Zn/Ti(OiPr)2Cl2 gives the corresponding (±)-2,3-diarylpiperazines in 73-83% yields with dl/meso ratio >99%: 1%. The (±)-2,3-diphenylpiperazine obtained in t
- Vairaprakash, Pothiappan,Periasamy, Mariappan
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- Synthesis of chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octane derivatives
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Racemic 2,3-diaryl-1,4-diazabicyclo[2.2.2]octane (DABCO) derivatives are synthesized from the readily accessible piperazines in 50-64% yield by cyclization using ethylene bromide, triethylamine, and KI at 80 °C. The enantiomerically enriched 2,3-diphenylpiperazine and the 2,3-bis(1-naphthyl)piperazine derivatives are prepared by a resolution method using commercially available optically active acids, yielding the corresponding DABCO derivatives in 51-64% yield with up to 99% ee. This mild cyclization can also be applied to enantiopure camphanyldiamine derivatives, and the products are obtained in 72-86% yields.
- Periasamy, Mariappan,Edukondalu, Athukuri,Reddy, Polimera Obula
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p. 3651 - 3655
(2015/04/22)
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- Diastereoselective synthesis of piperazines by manganese-mediated reductive cyclization.
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A simple and effective synthesis of trans aryl-substituted piperazines using a Bronsted acid and manganese(0) is described. [reaction: see text]
- Mercer, Gregory J,Sigman, Matthew S
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p. 1591 - 1594
(2007/10/03)
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- Electroorganic Chemistry. 129. Electroreductive Synthesis of Chiral Piperazines and Enantioselective Addition of Diethylzinc to Aldehydes in the Presence of the Chiral Piperazines
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Electroreduction of diimines, prepared from 1,2-diamines and aromatic aldehydes, in acidic media gave intramolecularly coupled products, 2,3-diarylpiperazines, stereoselectively.Chiral tri- and tetrasubstituted piperazines were synthesized effectively fro
- Shono, Tatsuya,Kise, Naoki,Shirakawa, Eiji,Matsumoto, Hideshi,Okazaki, Eiichi
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p. 3063 - 3067
(2007/10/02)
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