Home Physical Sciences Pyridopyridazines, Benzimidazolopyrimidines Triazolopyrimidines, 9-Oxo-2,3,6,7-tetraazabicyclo[3.3.1]nona-3,7-diene and Aroylcinnolines from 2-Arylhydrazono-3-oxopropanals
Article
Licensed
Unlicensed Requires Authentication

Pyridopyridazines, Benzimidazolopyrimidines Triazolopyrimidines, 9-Oxo-2,3,6,7-tetraazabicyclo[3.3.1]nona-3,7-diene and Aroylcinnolines from 2-Arylhydrazono-3-oxopropanals

  • EMAIL logo and
Published/Copyright: June 2, 2014
Become an author with De Gruyter Brill
Author Information Explore this Subject
Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 59 Issue 6

The reaction of the 2-arylhydrazonopropanal 3a with 2-amino1,1,3-tricyanopropene 4 afforded the pyridopyridazines 6. On the other hand, reaction of 3b with 4 afforded 7. Compounds 3a,b also condensed with 2-aminobenzimidazole and 3(5)-amino-1,2,4-triazole to yield azolopyrimidines 10 and 13. Refluxing compounds 3a,b in acetic acid in the presence of ammonium acetate afforded 2,3,6,7-tetraaza-bicyclo[3.3.1]nona-3,7-diene 14 and aroylcinnoline 15 respectively.

Keywords: 2-Arylhydrazonopropanals; Pyridopyridazines; Aminotriazole; Azolopyrimidines; Aroylcinnoline
Received: 2002-11-8
Published Online: 2014-6-2
Published in Print: 2004-6-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Neue Erdalkalimetall-reiche binäre Indide: Ca2In, Sr28In11 und Sr5In3 / New Alkaline Earth Rich Binary Indides: Ca2In, Sr28In11 und Sr5In3
  2. Syntheses and Crystal Structures of the Two New Polychalcogenides [Mn(C6H14N2)3]Se6 and [Mn(C6H14N2)3]2[C6H16N2](TeSe2)2Se
  3. Dimethyl-, Disilyl- and Digermylsulfide: Different Intermolecular Contacts in the Solid State
  4. Neue 3-Imidazolin-1-oxyl-Radikale mit pyridyl und chinolylhaltigen 4-(2-Aminovinyl)-Substituenten und Palladium, Platin und Ruthenium-Komplexe mit diesen 4-Amino-1-azadien-Liganden / New 3-Imidazoline-1-oxyl Radicals with Pyridyl and Quinolyl Containing 4-(2-Aminovinyl) Substituents and Palladium, Platinum and Ruthenium Complexes of these 4-Amino-1-aza-diene Ligands
  5. Square Planar Complexes of Cu(II) with an N2O Donor Set of a New Schiff Base Ligand: Synthesis and Structural Aspects
  6. Polysulfonylamine, CLXIX. Intermolekulare Wechselwirkungen in kristallinen Di(organosulfonyl)aminen. Teil 1. Di(4-brombenzolsulfonyl)amin: Zwei Konformationspolymorphe und Strukturverwandtschaft eines Polymorphs mit dem entsprechenden 2,4-Dimethylpyridinium-Salz / Polysulfonylamines, CLXIX. Intermolecular Interactions in Crystalline Di(organosulfonyl)- amines. Part 1. Di(4-bromobenzenesulfonyl)amine: Two Conformational Polymorphs and the Structural Relationship of one Polymorph to the Corresponding 2,4-Dimethylpyridinium Salt
  7. Die (1-Cyclohepta-2,4,6-trienyl)thiolato-verbrüuckten Zweikernkomplexe – Mn2(CO)8(μ2-SC7H7)2 und Mn2(CO)6(C≡NtBu)2(μ2-SC7H7)2 / The (1-Cyclohepta-2,4,6-trienyl)thiolato-Bridged Dinuclear Complexes Mn2(CO)8(μ2-SC7H7)2 and Mn2(CO)6(C≡NtBu)2(μ2-SC7H7)2
  8. Adducts of the Heavier Group 13 Element Halides with Aminoiminoboranes
  9. Hexaethyl-2,4-dicarba-nido-hexaborane(8), Deprotonation and Complexation Studied by NMR Spectroscopy and Density Functional Theory (DFT) Calculations
  10. Some Novel Amino Acid-Schiff Bases and their Complexes Synthesis, Characterization, Solid State Conductivity Behaviors and Potentiometric Studies
  11. Ultrasound-Promoted Reduction of Conjugated Enones, α-Diketones and Acyloins with NaBH4 under Aprotic Condition
  12. Reduction of Carbonyl Compounds with NaBH4 under Ultrasound Irradiation and Aprotic Condition
  13. Synthesis of 5-Methyl-1,2,3,4,5,6-hexahydrocyclopenta[g]carbazole-1,7- diones and Crotonyl-2-isopropyl-1-oxo-1,2,3,4-tetrahydrocarbazoles from 1-Oxo-1,2,3,4-tetrahydrocarbazoles by Friedel-Crafts Reaction
  14. 1,4-Bis(p-pentazolylphenyl)butan, 1-p-Azidophenyl-4-p-pentazolylphenyl- butan und 1,4-Bis(p-azidophenyl)butan / 1,4-Bis(p-pentazolylphenyl)butane, 1-p-Azidophenyl-4-p-pentazolylphenyl-butane and 1,4-Bis(p-azidophenyl)butane
  15. Pyridopyridazines, Benzimidazolopyrimidines Triazolopyrimidines, 9-Oxo-2,3,6,7-tetraazabicyclo[3.3.1]nona-3,7-diene and Aroylcinnolines from 2-Arylhydrazono-3-oxopropanals
https://doi.org/10.1515/znb-2004-0615
Keywords for this article
2-Arylhydrazonopropanals; Pyridopyridazines; Aminotriazole; Azolopyrimidines; Aroylcinnoline

Articles in the same Issue

  1. Neue Erdalkalimetall-reiche binäre Indide: Ca2In, Sr28In11 und Sr5In3 / New Alkaline Earth Rich Binary Indides: Ca2In, Sr28In11 und Sr5In3
  2. Syntheses and Crystal Structures of the Two New Polychalcogenides [Mn(C6H14N2)3]Se6 and [Mn(C6H14N2)3]2[C6H16N2](TeSe2)2Se
  3. Dimethyl-, Disilyl- and Digermylsulfide: Different Intermolecular Contacts in the Solid State
  4. Neue 3-Imidazolin-1-oxyl-Radikale mit pyridyl und chinolylhaltigen 4-(2-Aminovinyl)-Substituenten und Palladium, Platin und Ruthenium-Komplexe mit diesen 4-Amino-1-azadien-Liganden / New 3-Imidazoline-1-oxyl Radicals with Pyridyl and Quinolyl Containing 4-(2-Aminovinyl) Substituents and Palladium, Platinum and Ruthenium Complexes of these 4-Amino-1-aza-diene Ligands
  5. Square Planar Complexes of Cu(II) with an N2O Donor Set of a New Schiff Base Ligand: Synthesis and Structural Aspects
  6. Polysulfonylamine, CLXIX. Intermolekulare Wechselwirkungen in kristallinen Di(organosulfonyl)aminen. Teil 1. Di(4-brombenzolsulfonyl)amin: Zwei Konformationspolymorphe und Strukturverwandtschaft eines Polymorphs mit dem entsprechenden 2,4-Dimethylpyridinium-Salz / Polysulfonylamines, CLXIX. Intermolecular Interactions in Crystalline Di(organosulfonyl)- amines. Part 1. Di(4-bromobenzenesulfonyl)amine: Two Conformational Polymorphs and the Structural Relationship of one Polymorph to the Corresponding 2,4-Dimethylpyridinium Salt
  7. Die (1-Cyclohepta-2,4,6-trienyl)thiolato-verbrüuckten Zweikernkomplexe – Mn2(CO)8(μ2-SC7H7)2 und Mn2(CO)6(C≡NtBu)2(μ2-SC7H7)2 / The (1-Cyclohepta-2,4,6-trienyl)thiolato-Bridged Dinuclear Complexes Mn2(CO)8(μ2-SC7H7)2 and Mn2(CO)6(C≡NtBu)2(μ2-SC7H7)2
  8. Adducts of the Heavier Group 13 Element Halides with Aminoiminoboranes
  9. Hexaethyl-2,4-dicarba-nido-hexaborane(8), Deprotonation and Complexation Studied by NMR Spectroscopy and Density Functional Theory (DFT) Calculations
  10. Some Novel Amino Acid-Schiff Bases and their Complexes Synthesis, Characterization, Solid State Conductivity Behaviors and Potentiometric Studies
  11. Ultrasound-Promoted Reduction of Conjugated Enones, α-Diketones and Acyloins with NaBH4 under Aprotic Condition
  12. Reduction of Carbonyl Compounds with NaBH4 under Ultrasound Irradiation and Aprotic Condition
  13. Synthesis of 5-Methyl-1,2,3,4,5,6-hexahydrocyclopenta[g]carbazole-1,7- diones and Crotonyl-2-isopropyl-1-oxo-1,2,3,4-tetrahydrocarbazoles from 1-Oxo-1,2,3,4-tetrahydrocarbazoles by Friedel-Crafts Reaction
  14. 1,4-Bis(p-pentazolylphenyl)butan, 1-p-Azidophenyl-4-p-pentazolylphenyl- butan und 1,4-Bis(p-azidophenyl)butan / 1,4-Bis(p-pentazolylphenyl)butane, 1-p-Azidophenyl-4-p-pentazolylphenyl-butane and 1,4-Bis(p-azidophenyl)butane
  15. Pyridopyridazines, Benzimidazolopyrimidines Triazolopyrimidines, 9-Oxo-2,3,6,7-tetraazabicyclo[3.3.1]nona-3,7-diene and Aroylcinnolines from 2-Arylhydrazono-3-oxopropanals
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Winner of the OpenAthens UX Award 2026
Winner of the OpenAthens UX Award 2026
Have an idea on how to improve our website?
Please write us.
© 2026 De Gruyter Brill
Downloaded on 19.3.2026 from https://www.degruyterbrill.com/document/doi/10.1515/znb-2004-0615/html
Scroll to top button