Multi Component Reactions under Increased Pressure: On the Mechanism of Formation of Pyridazino[5,4,3-de][1,6]naphthyridine Derivatives by the Reaction of Malononitrile, Aldehydes and 2-Oxoglyoxalarylhydrazones in Q-Tubes

Majdah A Al-Johani; Khadijah M Al-Zaydi; Sameera M Mousally; Norah F Alqahtani; Noha Hilmy Elnagdi; Mohamed H Elnagdi

doi:10.3390/molecules22122114

Multi Component Reactions under Increased Pressure: On the Mechanism of Formation of Pyridazino[5,4,3-de][1,6]naphthyridine Derivatives by the Reaction of Malononitrile, Aldehydes and 2-Oxoglyoxalarylhydrazones in Q-Tubes

Molecules. 2017 Dec 1;22(12):2114. doi: 10.3390/molecules22122114.

Authors

Majdah A Al-Johani¹, Khadijah M Al-Zaydi², Sameera M Mousally³, Norah F Alqahtani⁴, Noha Hilmy Elnagdi⁵, Mohamed H Elnagdi⁶

Affiliations

¹ Department of Chemistry, Faculty of Sciences-AL Faisaliah, King Abdulaziz University, Jeddah, P.O. Box 50918, Jeddah 21533, Saudi Arabia. moon98.1@hotmail.com.
² Department of Chemistry, Faculty of Sciences-AL Faisaliah, King Abdulaziz University, Jeddah, P.O. Box 50918, Jeddah 21533, Saudi Arabia. alzaydi_kh@yahoo.com.
³ Department of Chemistry, Faculty of Sciences-AL Faisaliah, King Abdulaziz University, Jeddah, P.O. Box 50918, Jeddah 21533, Saudi Arabia. smousally@kau.edu.sa.
⁴ Department of Chemistry, Faculty of Sciences-AL Faisaliah, King Abdulaziz University, Jeddah, P.O. Box 50918, Jeddah 21533, Saudi Arabia. Nalqahtani00123@kau.edu.sa.
⁵ Department of Organic Chemistry, Faculty of Pharmacy, Modern University for Technology and Information, Cairo, P.O. Box 12518, Cairo 11511, Egypt. elnagdinoha@yahoo.com.
⁶ Faculty of Science, Cairo University; Cairo, P.O. Box 12613, Cairo 11511, Egypt. m.h.elnagdi@outlook.com.

Abstract

Efficient synthesis of phenanthridin-6(5H)-one derivatives 12a-n in a four-component reaction of aldehyde hydrazone, aromatic aldehydes and malononitrile in Q-Tubes is reported. The results showed that the methodology has the advantage of being a one-pot synthesis of tricyclic systems in good yields. Potential routes leading to formation of compounds 12 are discussed. The structures of the synthesized compounds could be unequivocally established via X-ray crystal structure determination and spectroscopic methods.

Keywords: 2-amino-1,1,3-propenetricarbonitrile; X-ray crystallography; arylhydrazonals; negative activation volume; pyridazines.

MeSH terms

Aldehydes / chemistry*
Chemistry Techniques, Synthetic
Crystallography, X-Ray / methods
Hydrazones / chemistry*
Magnetic Resonance Spectroscopy / methods
Mass Spectrometry / methods
Molecular Structure
Naphthyridines / chemical synthesis*
Nitriles / chemistry*
Pressure*
Pyridazines / chemical synthesis*

Substances

Aldehydes
Hydrazones
Naphthyridines
Nitriles
Pyridazines
dicyanmethane