Multicomponent reactions under increased pressure: on the reaction of arylhydrazonals, aromatic aldehydes and malononitrile in Q-Tube

Kamal Usef Sadek; Maghraby Ali Selim; Abdul-Aziz Alnajjar; Mohamed Atallah; Mohamed Hilmy Elnagdi

doi:10.5155/eurjchem.7.4.468-472.1508

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Published: Dec 31, 2016

DOI: https://doi.org/10.5155/eurjchem.7.4.468-472.1508

Keywords:

Q-Tubes, Azaenamines, Arylhydrazonals, Biphenyl derivatives, Pyridazino naphthyridine, Reactions under high pressure

Section

Research Article

Issue

Vol. 7 No. 4 (2016): December 2016

Dates

Received 2016-11-11
Accepted 2016-12-03
Published 2016-12-31

Kamal Usef Sadek

Chemistry Department, Faculty of Science, Minia University, 61519, Minia, Egypt

Maghraby Ali Selim

Chemistry Department, Faculty of Science at Qena, South Valley University, 83512, Qena, Egypt

Abdul-Aziz Alnajjar

Applied Science Department, College of Technological Studies, Public Authority for Applied Education and Training, 13060, Safat, Kuwait

Mohamed Atallah

Chemistry Department, Faculty of Science at Qena, South Valley University, 83512, Qena, Egypt

Mohamed Hilmy Elnagdi

Chemistry Department, Faculty of Science, Cairo University, 12613, Giza, Egypt

Abstract

A novel multi-component reaction between arylhydrazonals, malononitrile and aromatic aldehydes under high pressure utilizing Q-tube was carried out. The reaction of arylhydrazonal (1j) with malononitrile and aromatic aldehydes afforded the corresponding biphenyl derivatives (4). However, compound 1h reacted with malononitrile and aromatic aldehydes (7) to afford pyridazino[5,4,3-de]1,6-naphthyridine-7-carbonitrile derivatives (8). In contrast, the arylhydrazonal (1k) at the same reaction conditions afforded the corresponding pyridazinoquinazoline derivative (22). A rationalization for the difference in behavior for reaction of compounds 1h-k with malononitrile and aromatic aldehydes was postulated. Based on these findings a mechanism to account for the formation of the reaction products is suggested excluding possible initial dimerization of malononitrile as has been previously reported.

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Sadek, K. U.; Selim, M. A.; Alnajjar, A.-A.; Atallah, M.; Elnagdi, M. H. Multicomponent Reactions under Increased Pressure: On the Reaction of Arylhydrazonals, Aromatic Aldehydes and Malononitrile in Q-Tube. Eur. J. Chem. 2016, 7, 468-472.

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References

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Supporting Agencies

Minia University, 61519, Minia, Egypt and College of Technological Studies, Public Authority for Applied Education and Training, 13060, Safat, Kuwait

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