- Cyclobutane-derived diamines: Synthesis and molecular structure
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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.,Pavlenko, Sergiy O.,Grygorenko, Oleksandr O.,Volochnyuk, Dmitriy M.,Shishkina, Svitlana V.,Shishkin, Oleg V.,Komarov, Igor V.
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scheme or table
p. 5941 - 5952
(2010/11/04)
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- Synthesis of 2-azaspiro[3.3]heptane-derived amino acids: Ornitine and GABA analogues
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Synthesis of 6-amino-2-azaspiro[3.3]heptane-6-carboxylic acid and 2-azaspiro[3.3]heptane-6-carboxylic acid was performed. Both four-membered rings in the spirocyclic scaffold were constructed by subsequent ring closure of corresponding 1,3-bis-electrophil
- Radchenko, Dmytro S.,Grygorenko, Oleksandr O.,Komarov, Igor V.
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experimental part
p. 515 - 521
(2010/11/04)
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