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SYNTHESIS OF SPIRO[2-CYCLOPENTENE-1,3 '-IMIDAZO[1,2-a]-PYRIDINE] DERIVATIVES AND THEIR INTERESTING BEHAVIOR IN H-1-NMR SPECTRA IN DEUTERIOCHLOROFORM

  作者 ABE TAKASHI; KAKEHI AKIKAZU; SUGA HIROYUKI; OKUMURA YUKIHISA; ITOH KENNOSUKE  
  选自 期刊  Heterocycles;  卷期  2010年81-9;  页码  2075-2086  
  关联知识点  
 

[摘要]Ethyl 2',3'-dihydro-2-methylthio-2',4-dioxospiro[2-cyclopentene-1,3'-imidazo[ 1,2-a]pyridine]-3-carboxylates were synthesized from the reactions of 3-[bis(methylthio)methylene]-2(3H)-imidazo[1,2-a]pyridinones with ethyl 4-chloroacetoacetate in the presence of a base. The 2-methylthio group in these Spiro compounds was easily replaced with some primary and secondary amines to afford the corresponding 2-amino derivatives. Very interestingly, the proton signals of these Spiro compounds in the H-1-NMR spectra in deuteriochloroform (CDCl3) changed with an increase in the sample concentration, and the analysis for the magnitude and the direction of each proton shift disclosed the conformational change of the cyclopentenone moiety in this molecule.

 
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