Preparation of new nitrogen-bridged heterocycles. 56. Syntheses and reactions of 1-[2,2-bis(alkylthio)-1-(ethoxycarbonylacetyl)vinyl]pyridinium salts.
The title compounds, readily available from the S-alkylation of pyridinium 1-[alkylthio(thiocarbonyl)](ethoxycarbonylacetyl)methylides with alkyl halides or alkyl bromoacetates, were treated with a base and then a dehydrogenating agent to provide some unique products such as 3-[bis(alkylthio)methylene]-2(3H)-indolizinones and dialkyl 7-methyl-4-oxo-1,4,8,8a-tetrahydro-1,4-thiazino[3,4,5-cd]indolizine-1,5-dicarboxylates. On the other hand, similar reaction of these pyridinium salts in the absence of the dehydrogenating agent afforded alkyl 2-hydroxyindlizine-3-carboxythiolates, whose yields were increased by adding trifluoroacetic acid to the reaction mixture. The structures of some products were confirmed by the X-ray analyses.
Kakehi
Akikazu
A
Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan. akakehi@gipwc.shinshu-u.ac.jp
Suga
Hiroyuki
H
Yamauchi
Yuuya
Y
Yasuraoka
Katsuaki
K
Kobayashi
Tomoshige
T
Ohta
Akira
A
D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000378:metabolism; D017672:Nitrogen Compounds / Q000138:chemical synthesis* / Q000378:metabolism; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000378:metabolism; D012492:Salts / Q000138:chemical synthesis* / Q000378:metabolism
D006571:Heterocyclic Compounds; D017672:Nitrogen Compounds; D011726:Pyridinium Compounds; D012492:Salts