3873-79-8Relevant academic research and scientific papers
Continuous flow photochemistry as an enabling synthetic technology: Synthesis of substituted-6(5: H)-phenanthridinones for use as poly(ADP-ribose) polymerase inhibitors
Fang,Tranmer
supporting information, p. 720 - 724 (2016/05/19)
Methods utilizing continuous flow photochemistry, an enabling synthetic technology, have been developed for the generation of phenanthridinones via an intramolecular photochemical cyclization of 2-chlorobenzamides for the purposes of generating poly(ADP-ribose) polymerase inhibitors. Herein we report 16 examples of a single-step flow photocyclization which produces substituted phenanthridinones in yields up to 99%, while a two-step method leads directly to phenanthridinones from 2-chlorobenzoyl chlorides and anilines via a novel continuous flow amidation/photocyclization protocol. Overall, the flow photocyclization reactions typically progress in good to excellent yields, and in a superior fashion to analogous batch methods, greatly enabling the drug discovery process.
DIARYL PYRIMIDINONES AND RELATED COMPOUNDS
-
Page/Page column 39, (2008/06/13)
Compounds of Formula (I) are provided. In which the variables are as described herein. Such compounds may be used to modulate CB 1 activity in vivo or in vitro, and are particularly useful in the treatment of conditions responsive to CB 1 modulation in hu
Photocyclization of Aryl Halides. Part 3. Phenanthridone Photosynthesis from 2-Halogenobenzanilides
Grimshaw, James,Silva, A. Prasanna de
, p. 857 - 866 (2007/10/02)
2-Chlorobenzanilides cyclize to phenanthridones in deaereted cyclohexane solution on 254 nm irradiation, whereas 2-bromo- and 2-iodo-benzanilides undergo dehalogenative reduction.These observations are understandable in terms of the assisted homolysis model as applied to configurationally flexible molecules.Cyclization in hydrocarbon media is retarted by triplet quenchers and fails in polar solvents.The cyclization can also be singlet and triplet sensitized. 4'-Substituents influence the cyclization quantum yield by altering the ?-donor ability of the aniline ring and the rotational barrier about the amide bond.
