Cyclobutane-derived diamines: synthesis and molecular structure.
Cyclobutane diamines (i.e., cis- and trans-1,3-diaminocyclobutane, 6-amino-3-azaspiro[3.3]heptane, and 3,6-diaminospiro[3.3]heptane) are considered as promising sterically constrained diamine building blocks for drug discovery. An approach to the syntheses of their Boc-monoprotected derivatives has been developed aimed at the preparation of multigram amounts of the compounds. These novel synthetic schemes exploit classical malonate alkylation chemistry for the construction of cyclobutane rings. The conformational preferences of the cyclobutane diamine derivatives have been evaluated by X-ray diffraction and compared with the literature data on sterically constrained diamines, which are among the constituents of commercially available drugs.
Radchenko
Dmytro S
DS
Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska Street 64, Kyiv 01033, Ukraine.
Pavlenko
Sergiy O
SO
Grygorenko
Oleksandr O
OO
Volochnyuk
Dmitriy M
DM
Shishkina
Svitlana V
SV
Shishkin
Oleg V
OV
Komarov
Igor V
IV
D018360:Crystallography, X-Ray; D003503:Cyclobutanes / Q000737:chemistry*; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D003503:Cyclobutanes; D003959:Diamines