Preparation of new nitrogen-bridged heterocycles. 49. A new access to thieno[3,4-b]indolizine derivatives.
The title compounds, together with 3-vinylindolizine-1-carbonitriles (4-56%), were prepared in 1-18% yields from the S-alkylation of pyridinium 1-[3-ethoxycarbonyl-1-[cyanomethylthio(thiocarbonyl)]]all ylides with alkyl halides, followed by treatment of the resulting pyridinium salts with a base and then a dehydrogenating agent. In several reactions of pyridinium salts obtained from reaction of the allylides with benzylic halides, trace amounts of bis[1-cyano-9-(ethoxycarbonyl)thieno[3,4-b]indolizin-3-yl] disulfides with an interesting superimposed structure were also isolated. The structures of these compounds were confirmed by X-ray analyses.
Kakehi
A
A
Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, Wakasato, Nagano, Japan. akakehi@gipwc.shinshu-u.ac.jp
Ito
S
S
Hirata
K
K
Zuo
P
P
D003461:Crystallography; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007212:Indolizines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013876:Thiophenes / Q000737:chemistry*
D006571:Heterocyclic Compounds; D007212:Indolizines; D013876:Thiophenes; D009584:Nitrogen