Chemical Research in Chinese Universities ›› 2005, Vol. 21 ›› Issue (3): 274-279.

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Differentiation of Constitutional Isomer of 2,2a,3,4-Tetrahydro-4-methyl-2a-phenyl-2-(thiophen-2-yl)-1H-azeto[2,1-d][1,5]benzothiazepin-1-one-5-oxide and Fragmentations of 2,3-Dihydro-2,4-diphenyl-1,5-benzothiazepine-1-oxide/-1,1-dioxide

XU Jia-xi, ZUO Gang, LIANG Bo   

  1. Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China
  • Received:2004-06-17 Online:2005-05-24 Published:2011-08-06
  • Supported by:

    Supported by the National Natural Science Foundation of China(No.20272002).

Abstract: Mass spectrometric behaviour of 2,2a,3,4-tetrahydro-4-methyl-2a-phenyl-2-(thiophen-2-yl)-1H-azeto[2,1-d][1,5]benzothiazepin-1-one-5-oxide and 2,3-dihydro-2,4-diphenyl-1,5-benzothiazepine-1-oxide/-1,1-dioxide have been studied with the aid of mass-analyzed ion kinetic energy spectrometry and accurate mass measurements under electron impact ionization. The monooxide derivatives showed a tendency to eliminate an alkene or an oxygen atom. 1H-Azeto[2,1-d][1,5]benzothiazepin-1-one-5-oxide could also eliminate the thiophen-2-ylketene molecule via a reverse [2+2] cycloaddition. 2,3-Dihydro-2,4-diphenyl-1,5-benzothiazepine-1-oxide/-1,1-dioxide could eliminate SO2 or SO, respectively. The structure of 2,2a,3,4-tetrahydro-4-methyl-2a-phenyl-2-(thiophen-2-yl)-1H-azeto[2,1-d][1,5]benzothiazepin-1-one-5-oxide was identified on the basis of its fragmentation. The identification was supported by the fragmentations of model compound, 2,3-dihydro-2,4-diphenyl-1,5-benzothiazepine-1-oxide/-1,1-dioxide.

Key words: 1H-Azeto[2,1-d][1,5]benzothiazepin-1-one, 1,5-Benzothiazepine, Lactam, Mass spectrometry