68372-66-7Relevant academic research and scientific papers
Synthesis of 3,4-fused cycloalkanopyrroles by 1,3-dipolar cycloaddition
Kelly, James M.,Leeper, Finian J.
, p. 819 - 821 (2012/03/10)
The synthesis of a number of 3,4-fused cycloalkanopyrroles bearing substituents on the cycloalkane ring was accomplished by 1,3-dipolar cycloaddition. The yield of the cyclization appeared to depend on the base-sensitivity of the Michael acceptor, but the method is applicable across a broad range of cyclic α,β-unsaturated ketone esters. Functional group transformations can be undertaken following pyrrole synthesis to increase the diversity of cycloalkanopyrroles accessible by this method. One pyrrole thus made is a diester of a conformationally-constrained analogue of porphobilinogen, the precursor of the natural tetrapyrroles.
Synthesis of 2,4-Diazabicyclooctane-3,7-diones and 3-Thioxo-2,4-diazabicyclooctan-7-one by an Intramolecular Michael-type Reaction. Stability of 2,4 Diaza-, 4-Oxa-2-aza-, and 4-Thia-2-aza-bicyclooctane-3,7-diones
Harris, C. John
, p. 2497 - 2502 (2007/10/02)
Novel 2,4-diazabicyclooctane-3,7-diones (10) have been prepared by an intramolecular Micael-type cyclisation.The analogous 3-thioxo-2,4-diazabicyclooctan-7-one system (20) is obtained by base-catalysed retro-Michael reaction of the less stable 3-arylimino-2-thia-4-azabicyclooctan-7-one isomer (19).The 2-aza-4-oxabicyclooctane-3,7-dione system (17) is shown to be very unstable to base, fragmenting via the carbamic acid to give carbon dioxide and a 4-N-substituted cyclopent-2-enone (11).The relative stability to base of these bicyclic systems is correlated with their structure.
