Three distinct reactions of 3,4-dihydroisoquinolines with azlactones: novel synthesis of imidazoloisoquinolin-3-ones, benzo[a]quinolizin-4-ones, and benzo[d]azocin-4-ones.
A facile and direct synthetic entry to tricyclic imidazoloisoquinolin-3-ones and benzo[a]quinolizin-4-ones is reported based on the ring annulation of 1-unsubstituted and 1-substituted dihydroisoquinolines with azlactones under neutral conditions in a one-step procedure. Bicyclic 2,3-dihydrobenzo[d]azocin-4-ones were also prepared using simple azlactone and 1-substituted dihydroisoquinolines in a one-pot reaction. [reaction: see text]
Worayuthakarn
Rattana
R
Chulabhorn Research Institute, Vipavadee Rangsit Highway, Bangkok 10210, Thailand.
Thasana
Nopporn
N
Ruchirawat
Somsak
S
D000089:Acetic Anhydrides; D000818:Animals; D001392:Azocines / Q000138:chemical synthesis*; D001547:Benzaldehydes / Q000737:chemistry; D006626:Hippurates / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007546:Isoquinolines / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D011161:Porifera / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis*; D019346:Sodium Acetate / Q000737:chemistry; D013237:Stereoisomerism
D000089:Acetic Anhydrides; D001392:Azocines; D001547:Benzaldehydes; D006626:Hippurates; D007093:Imidazoles; D007202:Indicators and Reagents; D007546:Isoquinolines; D007783:Lactones; D011807:Quinolizines; C031800:acetic anhydride; D019346:Sodium Acetate; C030514:hippuric acid