Synthesis of some new 2-cyano-N'-(2-hydroxy-5-(4-methylphenyl diazenyl)benzylidene)acetohydrazides and coumarin derivative
Hafez, S., Elrayes, S., Hanafy, N. (2024). Synthesis of some new 2-cyano-N'-(2-hydroxy-5-(4-methylphenyl diazenyl)benzylidene)acetohydrazides and coumarin derivative. EKB Journal Management System, 6(1), 1-9. doi: 10.21608/aels.2024.288551.1056
Sara Ahmed Hafez; Samir Elrayes; Nadia Hanafy. "Synthesis of some new 2-cyano-N'-(2-hydroxy-5-(4-methylphenyl diazenyl)benzylidene)acetohydrazides and coumarin derivative". EKB Journal Management System, 6, 1, 2024, 1-9. doi: 10.21608/aels.2024.288551.1056
Hafez, S., Elrayes, S., Hanafy, N. (2024). 'Synthesis of some new 2-cyano-N'-(2-hydroxy-5-(4-methylphenyl diazenyl)benzylidene)acetohydrazides and coumarin derivative', EKB Journal Management System, 6(1), pp. 1-9. doi: 10.21608/aels.2024.288551.1056
Hafez, S., Elrayes, S., Hanafy, N. Synthesis of some new 2-cyano-N'-(2-hydroxy-5-(4-methylphenyl diazenyl)benzylidene)acetohydrazides and coumarin derivative. EKB Journal Management System, 2024; 6(1): 1-9. doi: 10.21608/aels.2024.288551.1056

Synthesis of some new 2-cyano-N'-(2-hydroxy-5-(4-methylphenyl diazenyl)benzylidene)acetohydrazides and coumarin derivative

Advances in Environmental and Life Sciences
Volume 6, Issue 1, July 2024, Page 1-9  XML PDF (434.31 K)
Document Type: Original research articles
DOI: 10.21608/aels.2024.288551.1056
View on SCiNiTO View on SCiNiTO
Authors
Sara Ahmed Hafez1; Samir Elrayes email orcid 1; Nadia Hanafy email 2
1Chemistry department, Faculty of Sciences, Suez Canal University, Ismailia, Egypt
2chemistry, Cairo university
Abstract
A new ten heterocyclic compounds were prepared starting from aniline derivatives which underwent diazotization reaction with salicylaldehyde affording 5-tolyl azo salicylaldehyde 2 which further reacted with 2-isocyanoacetohydrazide to produce 2-cyano-N'-(2-hydroxy-5-(4-methyl phenyldiazenyl)benzylidene)acetohydrazide 4 in yield 82%. In order to obtain 2-Cyano-N'-(2-hydroxy-5-(p-tolyldiazenyl)benzylidene 6a-e, component 4 underwent condensation reaction with several aldehydes, including benzaldehyde, 4-methoxy benzaldehyde, 2,5-dimethoxy benzaldehyde, 4-chloro benzaldehyde, and 2,5-dichloro benzaldehyde. 2-Cyano-N'-(2-hydroxy-5-(p-tolyldiazenyl)benzylidene) (6a) in yield 83%, 3-phenylacrylo hydrazide acrylohydrazide-3-(4-methoxyphenyl) (6b) in yield 82%, 2-Cyano-3-(2,5-dimethoxyphenyl) acrylohydrazide N'-(2-hydroxy-5-(p-tolyldiazenyl)benzylide,3-(Chlorophenol) (6c) in yield 75%, 2-Cyano-3-(2,4-dichlorophenyl)- N' -(2-hydroxy-5-(p-tolyldiazenyl) benzylidene) (6d) in yield 78% and 2-cyano- N' -(2-hydroxy-5-(p-tolyldiazenyl) benzylidene) acrylohydrazide (6e) in yield 85%, respectively. Moreover, compound 4 combined with para toluedene and/or aniline to produce 2-Cyano-N'- (2-hydroxy-5-p-tolyldiazenyl) benzylidene-2- (phenyldiazenyl) aceto-hydrazide (8a) in yield 64% and 3.1.3.2.2-Cyano-N'- (2-hydroxy-5-p-tolyldiazenyl) benzylidene-2- (p-tolyldiazenyl) acetohydrazide (8b) in yield 67% respectively. In the end, compound 4 gave rise to N'-(2-hydroxy-5-(p-tolyldiazenyl)benzylidene)-2-oxo-2H-chromene-3-carbohydrazide (11a) in yield 69% and 6-Hydroxy-N'-(2-hydroxy-5-(p-tolyldiazenyl) benzylidene)-2-oxo-2H-chromene-3-carbohydrazide (11b) in yield 72% via reactions with o-hydroxybenzaldehydes and 2,4-dihydroxybenzaldehyde. Several analytical and spectroscopic techniques, including mass spectroscopy, infrared spectroscopy, carbon thirteen magnetic resonance spectroscopy, proton magnetic resonance spectroscopy, and elemental analysis, were used to illustrate the structures of all produced compounds.
Keywords
Cyanoacetohydrazides; benzylidene; coumarin derivative
Statistics
Article View: 84
PDF Download: 16