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Mass spectrometric studies of cis‐ and trans ‐1a,3‐disubstituted‐1,1‐dichloro‐4‐formyl‐1a, 2,3,4‐tetrahydro‐l H ‐azirino[1,2‐ a ]1,5]benzodiazepines
Author(s) -
JiaXi Xu,
XinYu Zhang,
Sheng Jin
Publication year - 2000
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20000180320
Subject(s) - chemistry , propyne , yield (engineering) , ring (chemistry) , phenylacetylene , ion , mass spectrometry , aziridine , medicinal chemistry , quinoxaline , pyran , styrene , photochemistry , organic chemistry , materials science , chromatography , metallurgy , catalysis , polymer , copolymer
The mass spectrometric behaviour of four cis‐ and trans‐ 1a,3‐disubstituted‐1,1‐dichloro‐4‐formyl‐1a,2,3,4‐tetrahydro‐1 H ‐azirino [1, 2‐ a ][1,5]benzodiazepines has been studied with the aid of mass‐analysed ion kinetic energy spectrometry and exact mass measurements under electron impact ionization. All compounds show a tendency to eliminate a chlorine atom from the aziridine ring, and then eliminate a neutral propene or styrene from the diazepine ring to yield azirino [1,2‐ b ][1,3] benzimidazole ions. These azirino [1,2‐ a ][1,5]‐benzodiazepimes can also eliminate HCl, or Cl plus HCl simultaneously to undergo a ring enlargement rearrangement to yield 1,6‐benzodiazocine ions, which further lose small molecular fragments, propyne or phenylacetylene, with rearrangement to give quinoxaline ions.