Literature DB >> 16018678

Mesoionic 1,3-oxazinium olates. rearrangement to acylketenes and 3-azabicyclo[3.1.1]heptanetriones.

Hassan Sheibani1, Paul V Bernhardt, Curt Wentrup.   

Abstract

Metastable but isolable mesoionic 1,3-oxazinium 4-olates 9d-f undergo ring opening to acylketenes 10 at or near room temperature. The ketenes undergo intramolecular criss-cross [2 + 2] cycloaddition to afford 3-azabicyclo[3.1.1]heptanetriones 12. The structure of 12d was established by X-ray crystallography.

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Year:  2005        PMID: 16018678     DOI: 10.1021/jo050428m

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  1 in total

1.  A convenient one-pot synthesis of 3-amino-2, 5-dihydropyridazine and pyrimidine derivatives in the presence of high surface area MgO as a highly effective heterogeneous base catalyst.

Authors:  Hassan Sheibani; Mohammad Ali Amrollahi; Zeinab Esfandiarpoor
Journal:  Mol Divers       Date:  2009-06-19       Impact factor: 2.943

  1 in total

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