Preparation of 2,3-Diphenyl quinoxaline
Experiment ( 6 )
Experiment ( 6 )
Preparation of 2,3-Diphenyl quinoxaline
Preparation of 2,3-Diphenyl quinoxaline
Practical Organic
Practical Organic
chemistry
chemistry
3
3
rd
rd
Stage
Stage
Salahaddin University – Erbil
College of Science
Chemistry Department
2022-2023
2022-2023
1
Prepared by Naween M. Yonus
•
Quinoxaline is an organic compounds formed
by the fusion of two aromatic rings, benzene
and pyrazine. For this reason is also called
benzopyrazine, and is described as a
bioisosteres
of quinoline, naphthalene and
benzothiophene.
2
•
Quinoxaline
is isomeric with other naphthyridines
including quinazoline, phthalazine and cinnoline.
It is a
colorless oil that melts just above room temperature.
•
Although quinoxaline itself is mainly of academic
interest, quinoxaline derivatives are used as dyes,
pharmaceuticals, and antibiotics such as olaquindox,
carbadox, echinomycin, levomycin and actinoleutin.
3
Chemistry of quinoxaline
4
•
Quinoxaline is a low melting solid and is miscible with water. It is
weakly basic pKa (0.56). Quinoxaline forms salt with acids.
Nitration occurs only under forcing condition (Conc. HNO
3
,
Oleum, 90C) to give 5-nitroquinoxaline(1.5%) and 5,7- dinitro –
quinoxaline (24%)
Reactions of quinoxaline:
90 C
5
•
Oxidation of quinoxaline result in the formation of the
product depending on the nature of the oxidizing agent
employed with alkaline potassium permanganate pyrazine
2,3-dicarboxylic acid is formed ,while with peracid quinoxaline
di-N-oxid results.
•
synthesis of quinoxaline derivatives via the
condensation of aryl 1, 2-diamines with 1, 2- dicarbonyl
compounds in EtOH at warm temperature in absence of
acid, base or catalytic support.
6
Synthesis of quinoxaline
2,3-diphenyl quinoxaline can be prepared by condensation
of benzyl with 1,2-phenlene diamine
7
Mechanism
8
9
Quinoxaline, an organic compound, is synthesized through the condensation of benzyl with 1,2-phenylene diamine in this practical organic chemistry experiment at Salahaddin University. Quinoxaline and its derivatives have various applications in dyes, pharmaceuticals, and antibiotics. The process involves reactions, oxidation, and detailed synthesis mechanisms to produce 2,3-diphenyl quinoxaline.
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Presentation Transcript
Practical Organic chemistry 3rd Stage Salahaddin University Erbil College of Science Chemistry Department Experiment ( 6 ) Preparation of 2,3-Diphenyl quinoxaline 2022-2023 Prepared by Naween M. Yonus 1
Quinoxaline is an organic compounds formed by the fusion of two aromatic rings, benzene and pyrazine. For this reason is also called benzopyrazine, and bioisosteres of quinoline, naphthalene and benzothiophene. is described as a 2
Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. It is a colorless oil that melts just above room temperature. Although quinoxaline itself is mainly of academic interest, quinoxaline derivatives are used as dyes, pharmaceuticals, and antibiotics such as olaquindox, carbadox, echinomycin, levomycin and actinoleutin. 3
Chemistry of quinoxaline Reactions of quinoxaline: Quinoxaline is a low melting solid and is miscible with water. It is weakly basic pKa (0.56). Quinoxaline forms salt with acids. Nitration occurs only under forcing condition (Conc. HNO3, Oleum, 90C) to give 5-nitroquinoxaline(1.5%) and 5,7- dinitro quinoxaline (24%) 90 C 4
Oxidation of quinoxaline result in the formation of the product depending on the nature of the oxidizing agent employed with alkaline potassium permanganate pyrazine 2,3-dicarboxylic acid is formed ,while with peracid quinoxaline di-N-oxid results. 5
Synthesis of quinoxaline synthesis condensation of aryl 1, 2-diamines with 1, 2- dicarbonyl compounds in EtOH at warm temperature in absence of acid, base or catalytic support. of quinoxaline derivatives via the 6
2,3-diphenyl quinoxaline can be prepared by condensation of benzyl with 1,2-phenlene diamine 7
