Cyclisation reactions of some pyridazinylimidoylketenes

Alexander P. Gaywood, Lawrence Hill, S. Haider Imam, Hamish McNab, Gabor Neumajer, William J. O'Neill, Peter Matyus

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

Flash vacuum pyrolysis (FVP) of aminopyridazinone derivatives of Meldrum's acid at 600 degrees C (0.02 Torr) results in generation of an imidoylketene intermediate followed by cyclisation. In the case of the 5-amino derivatives, the products are pyrido[2,3-d]pyridazines, whereas the 4-amino compounds lead to mixtures of pyrido[2,3-d]pyridazines and pyrrolo[3,2-c]pyridazines. The feasibility of the 1,5-sigmatropic shift of a chlorine atom, required for the formation of two of the pyrido[2,3-d]pyridazines, was supported by the corresponding reaction of a corresponding 2,6-dichloroaniline derivative. The feasibility of the decarboxylation mechanism required for the formation of the pyrrolo[3,2-c]pyridazines, was supported by related processes in the FVP reactions of model compounds and by DFT calculations.

Original languageEnglish
Pages (from-to)236-242
Number of pages7
JournalNew journal of chemistry
Volume34
Issue number2
DOIs
Publication statusPublished - 2010

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