134858-31-4Relevant academic research and scientific papers
The Synthesis of Novel N-Heterocycles from 2-Azido-, 2-Vinylazido- and 2-Formyl-1,6-Methanoannulene-2-carbaldehydes
Suschitzky, Hans,Kramer, Walter,Neidlein, Richard,Rosyk, Peter,Bohn, Thomas
, p. 923 - 927 (2007/10/02)
The preparation of 2-azido-1,6-methanoannulene 2 from 2-lithioannulene is described.The annulene 2 underwent ring expansion on thermolysis in the presence of various secondary amines to give novel bridged aza-annulenes of type 3 and also gave 1,3-dipolar addition products.When heated the vinyl azides 13 (R1 = R2 = H) and 13 underwent cyclisation to give the annulenopyrroles 14 and 15 respectively.Annulenopyridines such as 18 were obtained from the iminophosphorane 16 via an aza-Wittig reaction with phenyl or allyl isothiocyanate or tolyl isocyanate.Some 2-formyl derivatives 1 (R1 = CHO) when treated with tosylmethyl isocyanide yielded oxazolylannulenes 19.
