484654-44-6Relevant academic research and scientific papers
Enantioselective Synthesis of cis- A nd trans-Borocyclopropylmethanol: Simple Building Blocks to Access Heterocycle-Substituted Cyclopropylmethanols
Charette, André B.,Navuluri, Chandrasekhar,Siddiqui, Saher H.
, p. 3834 - 3846 (2019/10/11)
An enantioselective and non-oxidative methodology was developed to obtain enantioenriched cyclopropyl boronates using a diethanolamine-promoted selective decomplexation of dioxaborolane. The non-oxidative decomplexation of the dioxaborolane ligand from the cyclopropylmethoxide species formed in the dioxaborolane-mediated Simmons-Smith cyclopropanation reaction provided the enantio?-enriched CIDA-based (CIDA = N-cyclohexyliminodiacetic acid) boro?-cyclopropane in 92% yield and 95.6:4.4 er. A robustness screen has shown diethanolamine to be compatible with esters, carbamates and N-heterocycles, providing a tool to access enantioenriched cyclopropanes carrying not only base-sensitive but oxidizable functional groups as well. Diethanolamine was found to be compatible with the modified zinco-cyclopropanation reaction of allyl alcohol to remove residual dioxaborolane from the corresponding cis-N-heterocycle cyclopropylmethanol, thereby leading to improved yields.
Synthesis and pharmacological evaluation of some (pyridyl)cyclopropylmethyl amines and their methiodides as nicotinic receptor ligands.
Guandalini, Luca,Dei, Silvia,Manetti, Dina,Romanelli, Maria Novella,Scapecchi, Serena,Teodori, Elisabetta,Varani, Katia
, p. 487 - 496 (2007/10/03)
A series of 3- and (4-pyridyl)cyclopropylmethyl amines and their quaternary ammonium derivatives have been synthesized; they can be considered as rigid analogues of nicotine. The compounds have been tested on rat cerebral cortex to measure the affinity for the central nicotinic receptor. Only the methiodides show affinity in the micromolar range. The results obtained can provide useful information on the topography of the nicotinic receptor-binding site.
