A facile synthesis of cis-1-methyl-1,2,3,3a,4,8b- hexahydropyrrolo[3,2-f]pyrindine, an annulated nicotine analog.
[reaction: see text] The title compound, 2, has been synthesized in 45% overall yield in six steps from 3-bromopyridine. The hexahydropyrrolo[3,2-f]pyrindine skeleton was constructed from key intermediate 5, via intramolecular azomethine ylide-alkene [3 + 2] cycloaddition. The present work constitutes a general method for rapid assembly of other related tricyclic nicotine analogues.
Zhai
Hongbin
H
Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, China 200032. zhaih@pub.sioc.ac.cn
Liu
Peng
P
Luo
Shengjun
S
Fang
Fang
F
Zhao
Mingyue
M
D008024:Ligands; D015394:Molecular Structure; D009538:Nicotine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D011978:Receptors, Nicotinic / Q000378:metabolism; D013379:Substrate Specificity
C470810:1-methyl-1,2,3,3a,4,8b- hexahydropyrrolo(3,2-f)pyrindine; D008024:Ligands; D011725:Pyridines; D011758:Pyrroles; D011978:Receptors, Nicotinic; D009538:Nicotine