10603-48-2Relevant articles and documents
Preparation method of alkyl nitrile compound
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Paragraph 0131-0133, (2020/05/14)
The invention discloses a preparation method of an alkyl nitrile compound shown as formula I. The preparation method comprises the following step: in a solvent, in the presence of an additive and a catalyst, Zn (CN) 2 and an alkyl halide shown as formula II are subjected to a coupling reaction as shown in the specification to obtain the alkyl nitrile compound as shown in the formula I, wherein theadditive comprises an alkali, the catalyst comprises a nickel compound and a phosphine ligand; the nickel compound is one or more of zero-valent nickel, monovalent nickel salt and divalent nickel salt; when the nickel compound contains zero-valent nickel or divalent nickel salt, the catalyst further comprises a reducing agent. According to the preparation method disclosed by the invention, cyanation of an alkyl halide can be simply, conveniently and efficiently realized by using a cheap catalytic system, and the preparation method also has good functional group compatibility and substrate universality.
Novel 1-(azacyclyl)-3-arylsulfonyl-1H-pyrrolo[2,3-b]pyridines as 5-HT6 agonists and antagonists
Elokdah, Hassan,Li, David,McFarlane, Geraldine,Bernotas, Ronald C.,Robichaud, Albert J.,Magolda, Ronald L.,Zhang, Guo Ming,Smith, Deborah,Schechter, Lee E.
, p. 6208 - 6226 (2008/03/27)
1-Aminoethyl-3-arylsulfonyl-1H-indoles 1 are 5-HT6 receptor ligands with modest activity in a 5-HT6 cyclase assay. Introduction of an additional nitrogen in the indole ring provides 1-aminoethyl-3-arylsulfonyl-1H-pyrrolo[2,3-b]pyridines 2 with both enhanced 5-HT6 affinity and cyclase activity, many acting as 5-HT6 agonists. We constrained the basic side chain as part of a ring to make 1-(azacyclyl)-3-arylsulfonyl-1H-pyrrolo[2,3-b]pyridines incorporating a pyrrolidinyl 3 or piperidinyl 4 ring system. Preparation of compounds 3 and 4 required synthesis of the key intermediates, 1-(pyrrolidin-3-yl)-1H-pyrrolo[2,3-b]pyridines 7 and 1-(piperidin-3-yl)-1H-pyrrolo[2,3-b]pyridines 8, respectively. Intermediates 7 were prepared through alkylation of 7-azaindole while the intermediates 8 required an alternate synthesis. The compounds of both series 3 and 4 were shown to have high binding affinities for the 5-HT6 receptor. The in vitro functional activity at the 5-HT6 receptor varied depending on various functionalities including the selection of the arylsulfonyl, the substitution on the arylsulfonyl group, the ring size, and the substitution on the basic amine moiety producing either 5-HT6 receptor agonists or antagonists.
Stereocontrolled synthesis of 1,2-dialkyl-4-halopyrrolidines through PhSeX-induced cyclization of secondary homoallylamines
Outurquin, Francis,Pannecoucke, Xavier,Berthe, Benedicte,Paulmier, Claude
, p. 1007 - 1014 (2007/10/03)
The selenium-induced cyclization of α-alkyl or α,α-dialkylhomoallyl-benzylamines 1 by use of PhSeX (X = Cl, Br, I; 1.5 equiv.) provided a mixture of (phenylselanylmethyl)azetidines 2 and (phenylselanyl)pyrrolidines 3.[1] When an excess of PhSeX (X = Cl, Br) was used, 4-halopyrrolidines 4 (X = Cl) or 5 (X = Br) were formed and isolated in very good yields. Mono- or dialkyl 4-halopyrrolidines 4 and 5 could also be obtained stereospecifically by SO2Cl2 or Br2 treatment of 4-(phenylselanylmethyl)azetidines 2, by way of the intermediate (halomethyl)azetidines 14 (X = Cl) or 15 (X = Br). When starting from 4-(phenylselanyl)pyrrolidines 3, monoalkylated 4-halopyrrolidines 4 or 5 could be obtained stereospecifically after decomposition of the unstable dihaloselenuranes 16 and 17. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
