Cyclisation reactions of some pyridazinylimidoylketenes

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

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Flash vacuum pyrolysis (FVP) of aminopyridazinone derivatives of Meldrum's acid at 600 °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

Fingerprint

Pyridazines
Cyclization
Derivatives
Pyrolysis
Vacuum
Lead compounds
Discrete Fourier transforms
Chlorine
Atoms
Acids

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Materials Chemistry

Cite this

Gaywood, A. P., Hill, L., Imam, S. H., McNab, H., Neumajer, G., O'Neill, W. J., & Mátyus, P. (2010). Cyclisation reactions of some pyridazinylimidoylketenes. New Journal of Chemistry, 34(2), 236-242. https://doi.org/10.1039/b9nj00474b

Cyclisation reactions of some pyridazinylimidoylketenes. / Gaywood, Alexander P.; Hill, Lawrence; Imam, S. Haider; McNab, Hamish; Neumajer, Gabor; O'Neill, William J.; Mátyus, P.

In: New Journal of Chemistry, Vol. 34, No. 2, 2010, p. 236-242.

Research output: Contribution to journalArticle

Gaywood, AP, Hill, L, Imam, SH, McNab, H, Neumajer, G, O'Neill, WJ & Mátyus, P 2010, 'Cyclisation reactions of some pyridazinylimidoylketenes', New Journal of Chemistry, vol. 34, no. 2, pp. 236-242. https://doi.org/10.1039/b9nj00474b
Gaywood AP, Hill L, Imam SH, McNab H, Neumajer G, O'Neill WJ et al. Cyclisation reactions of some pyridazinylimidoylketenes. New Journal of Chemistry. 2010;34(2):236-242. https://doi.org/10.1039/b9nj00474b
Gaywood, Alexander P. ; Hill, Lawrence ; Imam, S. Haider ; McNab, Hamish ; Neumajer, Gabor ; O'Neill, William J. ; Mátyus, P. / Cyclisation reactions of some pyridazinylimidoylketenes. In: New Journal of Chemistry. 2010 ; Vol. 34, No. 2. pp. 236-242.
@article{5a69542e93074f0fa0753a5ecefd0a19,
title = "Cyclisation reactions of some pyridazinylimidoylketenes",
abstract = "Flash vacuum pyrolysis (FVP) of aminopyridazinone derivatives of Meldrum's acid at 600 °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.",
author = "Gaywood, {Alexander P.} and Lawrence Hill and Imam, {S. Haider} and Hamish McNab and Gabor Neumajer and O'Neill, {William J.} and P. M{\'a}tyus",
year = "2010",
doi = "10.1039/b9nj00474b",
language = "English",
volume = "34",
pages = "236--242",
journal = "New Journal of Chemistry",
issn = "1144-0546",
publisher = "Royal Society of Chemistry",
number = "2",

}

TY - JOUR

T1 - Cyclisation reactions of some pyridazinylimidoylketenes

AU - Gaywood, Alexander P.

AU - Hill, Lawrence

AU - Imam, S. Haider

AU - McNab, Hamish

AU - Neumajer, Gabor

AU - O'Neill, William J.

AU - Mátyus, P.

PY - 2010

Y1 - 2010

N2 - Flash vacuum pyrolysis (FVP) of aminopyridazinone derivatives of Meldrum's acid at 600 °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.

AB - Flash vacuum pyrolysis (FVP) of aminopyridazinone derivatives of Meldrum's acid at 600 °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.

UR - http://www.scopus.com/inward/record.url?scp=76149103866&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=76149103866&partnerID=8YFLogxK

U2 - 10.1039/b9nj00474b

DO - 10.1039/b9nj00474b

M3 - Article

AN - SCOPUS:76149103866

VL - 34

SP - 236

EP - 242

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 2

ER -