A new synthesis of indoloquinolizines by Pictet-Spengler reaction of tryptamine type 1,2-dihydropyridines utilizing sec-nitrodienamine.
The Pictet-Spengler reaction of tryptamine type 1,2-dihydropyridine 5c derived from the cycloaddition of the sec-nitrodienamine 3c with acetaldehyde afforded the indoloquinolizine derivatives 6 and 7.
Koike
T
T
Showa Pharmaceutical University, Machida, Tokyo, Japan. koike@ac.shoyaku.ac.jp
Shinohara
Y
Y
Tobinaga
S
S
Takeuchi
N
N
D002070:Butadienes / Q000737:chemistry*; D004095:Dihydropyridines / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009574:Nitro Compounds / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D014363:Tryptamines / Q000737:chemistry*
C423464:1-(2-(3-indolyl)ethylamino)-4-nitro-1,3-butadiene; D002070:Butadienes; D004095:Dihydropyridines; D007211:Indoles; D009574:Nitro Compounds; D011807:Quinolizines; D014363:Tryptamines; C030820:tryptamine; C038806:1,4-dihydropyridine