Synthesis of 6-aryl-6,6a,7,9a-tetrahydro-5H-cyclopenta[c] 1,7- and -1,8-phenanthrolines

Progress in the Chemistry of Tetrahydroquinolines

“…The diastereoselective synthesis of tetrahydro-1,7- and tetrahydro-1,8-phenanthroline derivatives 703 was achieved in moderate yields based on a TFA-catalyzed reaction between 5-aminoquinoline or 5-aminoisoquinoline 700 with aromatic aldehydes 701 and cyclopentadiene 702 in trifluoroethanol (Scheme ). Gore and co-workers also synthesized related 1,2,3,4-THQs involving a trifluoroacetic acid-catalyzed three-component Povarov reaction and investigated the structure–activity relationship of the synthesized tetrahydroquinoline as the membrane bound large-conductance, calcium-activated potassium channel (BKCa) agonists . The TFA-catalyzed approach was also extended to the synthesis of THQ-based nonsteroidal selective androgen receptor modulators (SARMs). , …”