Facile Synthesis of 3-Amino-2,5-dihydropyridazines and 4-Deazatoxoflavin Analogues via [3 + 3] Atom Combination: Approaches to Pyridazine Incorporating Pyrazole Moiety

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Original languageEnglish
Pages (from-to)473-479
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume54
Issue number1
Publication statusPublished - Jan 2017

Abstract

Arylhydrazones are prepared and reacted with pyrazolylmethylene malononitrile derivatives yielding 2,5-dihydropyridazines substituted at C-5 by pyrazole derivatives. Utilizing azaenamine containing a cyano group at the ortho position enabled the formation of the condensed pyridazino[1,6-a]quinazoline derivatives. A subsequent acetylation of the synthesized pyridazines led to the formation of pyrimido[4,5-c]pyridazine compounds which can be considered as 4-deazatoxoflavin derivatives. All the new compounds were full-characterized by the different spectral tools and the unambiguous structural elucidation of 2,5-dihydropyridazines was done using 2D-HMBC spectroscopy.

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Facile Synthesis of 3-Amino-2,5-dihydropyridazines and 4-Deazatoxoflavin Analogues via [3 + 3] Atom Combination: Approaches to Pyridazine Incorporating Pyrazole Moiety. / Abdelmoniem, Amr M.; Ghozlan, Said A.S.; Butenschön, Holger et al.
In: Journal of Heterocyclic Chemistry, Vol. 54, No. 1, 01.2017, p. 473-479.

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abstract = "Arylhydrazones are prepared and reacted with pyrazolylmethylene malononitrile derivatives yielding 2,5-dihydropyridazines substituted at C-5 by pyrazole derivatives. Utilizing azaenamine containing a cyano group at the ortho position enabled the formation of the condensed pyridazino[1,6-a]quinazoline derivatives. A subsequent acetylation of the synthesized pyridazines led to the formation of pyrimido[4,5-c]pyridazine compounds which can be considered as 4-deazatoxoflavin derivatives. All the new compounds were full-characterized by the different spectral tools and the unambiguous structural elucidation of 2,5-dihydropyridazines was done using 2D-HMBC spectroscopy.",
author = "Abdelmoniem, {Amr M.} and Ghozlan, {Said A.S.} and Holger Butensch{\"o}n and Abdelhamid, {Ismail A.}",
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T2 - Approaches to Pyridazine Incorporating Pyrazole Moiety

AU - Abdelmoniem, Amr M.

AU - Ghozlan, Said A.S.

AU - Butenschön, Holger

AU - Abdelhamid, Ismail A.

N1 - Publisher Copyright: © 2016 Wiley Periodicals, Inc. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2017/1

Y1 - 2017/1

N2 - Arylhydrazones are prepared and reacted with pyrazolylmethylene malononitrile derivatives yielding 2,5-dihydropyridazines substituted at C-5 by pyrazole derivatives. Utilizing azaenamine containing a cyano group at the ortho position enabled the formation of the condensed pyridazino[1,6-a]quinazoline derivatives. A subsequent acetylation of the synthesized pyridazines led to the formation of pyrimido[4,5-c]pyridazine compounds which can be considered as 4-deazatoxoflavin derivatives. All the new compounds were full-characterized by the different spectral tools and the unambiguous structural elucidation of 2,5-dihydropyridazines was done using 2D-HMBC spectroscopy.

AB - Arylhydrazones are prepared and reacted with pyrazolylmethylene malononitrile derivatives yielding 2,5-dihydropyridazines substituted at C-5 by pyrazole derivatives. Utilizing azaenamine containing a cyano group at the ortho position enabled the formation of the condensed pyridazino[1,6-a]quinazoline derivatives. A subsequent acetylation of the synthesized pyridazines led to the formation of pyrimido[4,5-c]pyridazine compounds which can be considered as 4-deazatoxoflavin derivatives. All the new compounds were full-characterized by the different spectral tools and the unambiguous structural elucidation of 2,5-dihydropyridazines was done using 2D-HMBC spectroscopy.

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