831176-42-2Relevant academic research and scientific papers
Cyclobutane ring opening reactions of 1,2,2a,8b-tetrahydrocyclobuta[c]- quinolin-3(4H)-ones
Selig, Philipp,Bach, Thorsten
, p. 2177 - 2182 (2008)
Two pathways are presented, which allow for the selective cleavage of the C1/C8b bond in the title compounds. The first reaction was found by serendipity when reductive debenzylation was attempted on a heteroanellated azabicyclo[4.2.0]octane. It yielded an eight-membered lactam ring (azocane). The second transformation relies on a rationally designed 1,2-rearrangement reaction, which was introduced because attempts to induce classical Wagner-Meerwein-type 1,2-shifts did not meet with success. The reaction, a retro-benzilic acid rearrangement, allowed for the conversion of a heteroanellated hydroxycyclobutanecarboxylate into the respective cyclopentadione (76% yield). Georg Thieme Verlag Stuttgart.
Photochemistry of 4-(2′-aminoethyl)quinolones: Enantioselective synthesis of tetracyclic tetrahydro-1aH-pyrido[4′,3′:2,3]- cyclobuta[1,2-c] quinoline-2,11(3H,8H)-diones by intra- and intermolecular [2 + 2]-photocycloaddition reactions in solution
Selig, Philipp,Bach, Thorsten
, p. 5662 - 5673 (2007/10/03)
Enantioselective [2 + 2]-photocycloaddition reactions on 4-(2′-aminoethyl)quinolones in solution were studied using the enantiomerically pure complexing agent 1 as source of chirality. The intermolecular reactions of fully N-protected substrates 5a-5c wit
Stereoselective intra- and intermolecular [2+2] photocycloaddition reactions of 4-(2′-aminoethyl)quinolones
Brandes, Sebastian,Selig, Philipp,Bach, Thorsten
, p. 2588 - 2590 (2007/10/03)
The 4-(2′-aminoethyl)quinolones 6, 8 and 9 were prepared starting from 4-(2′-bromoethyl)quinolone (4) in two steps and overall yields of 56-93%. They underwent inter- and intramolecular [2+2] photocycloaddition reactions with an alkene to provide the cycl
