- Straightforward access to cyclic amines by dinitriles reduction
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1,1,3,3-Tetramethyldisiloxane (TMDS) and polymethylhydrosiloxane (PMHS), when associated with titanium(IV) isopropoxide, provide two convenient systems for the reduction of nitriles into the corresponding primary amines. Kinetics of the two systems have been studied by 1H NMR and demonstrated that reduction with PMHS occurs faster than with TMDS. These two titanium-based systems reduce both aromatic and aliphatic nitriles in the presence of Br, CC, NO2, OH, and cyclopropyl-ring. In the case of cyclopropyl-nitriles, the formation of secondary amines, which come from an intermolecular reductive alkylation reaction was observed. This result was exploited for the reduction of dinitriles, which led, in one-step, to azepane, piperidine, pyrrolidine, and azetidine derivatives through an intramolecular reductive alkylation reaction.
- Laval, Stéphane,Dayoub, Wissam,Pehlivan, Leyla,Métay, Estelle,Favre-Reguillon, Alain,Delbrayelle, Dominique,Mignani, Gérard,Lemaire, Marc
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supporting information
p. 975 - 983
(2014/01/23)
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- Ru/C catalyzed cyclization of linear α,ω-diamines to cyclic amines in water
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A facile and convenient way to prepare cyclic amines in water was achieved by the catalyst system composed of Ru/C and Al powder. The α,ω-diaminoalkanes, 1,4-diaminobutane, 1,5-diaminopentane, and 1,6-diamino-heptane were converted to corresponding cyclic amines in good yields. The use of D2O provided a novel route to obtain deuterated cyclic amines in good yields.
- G?dda, Thomas M.,Yu, Xiao-Yan,Miyazawa, Akira
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experimental part
p. 1249 - 1253
(2010/03/30)
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