Gas-phase pyrolysis of 1-(2-azidophenyl)imidazole

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Alexander J. Blake, Bernard A. J. Clark, Hamish McNab and Craig C. Sommerville


Abstract

Flash vacuum pyrolysis (FVP) of the azide 4 leads to imidazo[1,2-a]benzimidazole 8 exclusively, via highly regioselective insertion of the triplet nitrene intermediate 5 into the 2-CH bond of the imidazole ring. The X-ray crystal structure and NMR spectroscopic properties of 8 are discussed in detail.


References

  1. B. A. J. Clark, H. McNab and C. C. Sommerville, Chem. Commun., 1996, 1211 RSC.
  2. J. M. Lindley, I. M. McRobbie, O. Meth-Cohn and H. Suschitzky, J. Chem. Soc., Perkin Trans. 1, 1977, 2194 RSC.
  3. For example, M. R. Grimmett, in Comprehensive Heterocyclic Chemistry, ed. K. T. Potts, Pergamon, Oxford, 1984, vol. 5, p. 418 Search PubMed.
  4. R. E. Busby, M. A. Khan, M. R. Khan, J. Parrick, C. J. G. Shaw and M. Iqbal, J. Chem. Soc., Perkin Trans. 1, 1980, 1427 RSC.
  5. H. Ogura, H. Takayanagi, Y. Yamazaki, S. Yonezawa, H. Takagi, S. Kobayashi, T. Kamioka and K. Kamoshita, J. Med. Chem., 1972, 15, 923 CrossRef CAS.
  6. For example, G. S. Reddy, L. Mandell and J. H. Goldstein, J. Chem. Soc., 1963, 1414 Search PubMed.
  7. S. Martinez-Carrera, Acta Crystallogr., 1966, 20, 783 CrossRef CAS.
  8. For example, H. McNab, J. Chem. Soc., Perkin Trans. 1, 1987, 657 Search PubMed.
  9. A. J. Arduengo III, H. V. R. Dias, R. L. Harlow and M. Kline, J. Am. Chem. Soc., 1992, 114, 5530 CrossRef CAS.
  10. J. Cosier and A. M. Glazer, J. Appl. Crystallogr., 1986, 19, 105 CrossRef CAS.
  11. G. M. Sheldrick, SHELXS-86, Acta Crystallogr., Sect. A, 1990, 46, 467 CrossRef.
  12. G. M. Sheldrick, SHELXL-93, University of Göttingen, Germany, 1993.
  13. G. M. Sheldrick, SHELXTL/PC ver. 4.3, Siemens Analytical Instrumentation Inc., Madison, WI.
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