Synthesis of Benzoxazine
Lady Jewellyn G.Diola*, Jennika Joy L. Casin, Andrian R. De Leon, Jan Rotsen Kyle A. Delos Santos
Department of Chemistry, College of Science
*Lady Jewellyn G. Diola; ladyjewellyndiola@yahoo.com
Abstract
Synthesis of 3,4-dihydro-3-(p-methylphenyl)-1,2-(2h)-benzoxazine involves the nucleophillic addition of the 1 °amine group upon the carbonyly group of the salicylaldehyde, the reduction of imine to amine and the addition of paraformaldehyde to proceed ring closure. The experiment prepared the product through Mannich reaction, a multicomponent condensation synthesis between ketone, aldehydes, enols and amines. Biosynthesis of benzoaxazines occur under reductive and nucleophilic reaction conditions. Formation of a Schiff base is necessary to perform first before reductive amination is performed. % yield of 3,4-dihydro-3-(p-methylphenyl)-1,2-(2h)-benzoxazinewas obtained from the reaction.
Keywords: Condensation Reactions, Mannich Reaction, Nucleophilic addition, Schiff Base, Reductive Amination.
Introduction
Benzoxazines are a class of oxygen-nitrogen heterocyclic compounds bearing different biological activities. These activities include antimicrobial, antifungal, antiangiogenic, therapeutic agents, antiarrhythmic, neuropeptide, antagonists, neuroprotective agents, estrogen receptorβ, agonists, and antimycobacterial agents. Compounds which are enolic react with a mixture of an aldehyde and a primary or secondary amine in the presence of an acid to yield an aminomethyl derivative (Norman, R. 1993). The multi component condensation of an aldehyde with an amine is called Mannich reaction. Mannich reaction is primarily a complex condensation reaction where 2 moieties or molecules combine to form a larger molecule. For the experiment, a two step linear reaction was observed: 1) condensation reaction to yield the Schiff base and 2) ring closure reaction.
A Schiff base is obtained from amine and ketone or aldehyde
Department of Chemistry, College of Science
*Lady Jewellyn G. Diola; ladyjewellyndiola@yahoo.com
Abstract
Synthesis of 3,4-dihydro-3-(p-methylphenyl)-1,2-(2h)-benzoxazine involves the nucleophillic addition of the 1 °amine group upon the carbonyly group of the salicylaldehyde, the reduction of imine to amine and the addition of paraformaldehyde to proceed ring closure. The experiment prepared the product through Mannich reaction, a multicomponent condensation synthesis between ketone, aldehydes, enols and amines. Biosynthesis of benzoaxazines occur under reductive and nucleophilic reaction conditions. Formation of a Schiff base is necessary to perform first before reductive amination is performed. % yield of 3,4-dihydro-3-(p-methylphenyl)-1,2-(2h)-benzoxazinewas obtained from the reaction.
Keywords: Condensation Reactions, Mannich Reaction, Nucleophilic addition, Schiff Base, Reductive Amination.
Introduction
Benzoxazines are a class of oxygen-nitrogen heterocyclic compounds bearing different biological activities. These activities include antimicrobial, antifungal, antiangiogenic, therapeutic agents, antiarrhythmic, neuropeptide, antagonists, neuroprotective agents, estrogen receptorβ, agonists, and antimycobacterial agents. Compounds which are enolic react with a mixture of an aldehyde and a primary or secondary amine in the presence of an acid to yield an aminomethyl derivative (Norman, R. 1993). The multi component condensation of an aldehyde with an amine is called Mannich reaction. Mannich reaction is primarily a complex condensation reaction where 2 moieties or molecules combine to form a larger molecule. For the experiment, a two step linear reaction was observed: 1) condensation reaction to yield the Schiff base and 2) ring closure reaction.
A Schiff base is obtained from amine and ketone or aldehyde
References: Mohrig, J., Hammond, C.N., Schatz, P. & Morril, T. Modern Projects and Experiments in Organic Chemistry: Miniscale and Standard Taper Microscale; W.H. Freeman and Company : New York, 2011. Norman, R ; Coxon, J. Principles of organic synthesis. Chapman & Hall ; UK, 1993 ; pp 251-267, 375-383.