273206-92-1Relevant articles and documents
Practical Synthesis of a 6-Triazolylazabicyclo[3.1.0]hexane
Sirois, Lauren E.,Xu, Jie,Angelaud, Remy,Lao, David,Gosselin, Francis
, p. 728 - 735 (2018/06/26)
We describe a practical, scalable synthesis of an advanced heterocyclic intermediate, (1R,5S,6s)-6-(4H-1,2,4-triazol-4-yl)-3-azabicyclo[3.1.0]hexane. A robust synthetic sequence based on a Kulinkovich-de Meijere pyrroline cyclopropanation followed by tran
2-AMINO PYRIDINE COMPOUNDS
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Page/Page column 77-79, (2008/12/05)
The present invention is directed to 2-aminopyrimidine compounds and pharmaceutically acceptable salts thereof, their synthesis and their use as HSP-90 inhibitors.
Mono- and disubstituted N,N-dialkylcyclopropylamines from dialkylformamides via ligand-exchanged titanium - Alkene complexes
De Meijere, Armin,Williams, Craig M.,Kourdioukov, Alexandre,Sviridov, Sergei V.,Chaplinski, Vladimir,Kordes, Markus,Savchenko, Andrei I.,Stratmann, Christian,Noltemeyer, Mathias
, p. 3789 - 3801 (2007/10/03)
Dibenzylformamide was treated with cyclohexylmagnesium bromide in the presence of either titanium tetraisopropoxide or methyltitanium triisopropoxide and a variety of cyclic and acyclic alkenes and alkadienes to give new mono- and disubstituted as well as bicyclic dialkylcyclopropylamines (Tables 1-3) in yields ranging from 18 to 90% (in most cases around 55%). 3-Benzyl-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane (10a) and the orthogonally bisprotected 3-tert-butoxycarbonyl-6-(N,N-dibenzyl)- 3-azabicyclo[3.1.0]hexane (10d) as well as the analogous 6-(N,N-dibenzylamino)bicyclo[3.1.0]hexane (12) were obtained as pure exo diastereomers in particularly high yields (87, 90, and 88%, respectively) from N-benzylpyrroline (15a), N-Boc-pyrroline (15d; Boc = tert-butyloxycarbonyl) and cyclopentene (19). 1,3-Butadiene (52) and substituted 1,3-butadienes were also aminocyclopropanated quite well to give 2-ethenylcyclopropylamines in good yields (51-64%). Except for alkenyl and aryl-substituted compounds, N,N-dibenzylcyclopropylamines can be debenzylated by catalytic hydrogenation to the primary cyclopropylamines as demonstrated for 10a and 10d to yield the fully deprotected 10e (93%) and mono-Boc-protected 10f (98%), respectively. The latter are interesting templates for combinatorial syntheses of libraries of small molecules with a well defined distance of 4.3 A between two nitrogen atoms.