Staff Members - Benha University
Studies on 4H-3,1-Benzoxazin-4-ones. A convenient synthesis of novel heterocycles with antimicrobial activity
• 2016
Publication Information
Authors
Esraa A. Abdel Wahab1, Wasfy2 F. A. A., Aly A. A.2,Elhefnawy M. Manal1
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publication.type
International
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Supplementary Materials
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Abstract
ABSTRACT
N-(2-(4-chlorophenyl)-1-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)vinyl)-2-(1,3-dioxoisoindolin-2-yl)acetamide 2 has been synthesized by treatment of anthranilic acid with (Z)-2-((4-(4-chlorobenzylidene)-5-oxo-4,5-dihydrooxazol-2-yl)methyl)isoindoline-1,3-dione 1 in boiling butanol. The reaction of 2 with nitrogen and carbon nucleophiles and with carbon electrophiles have been investigated.
INTRODUCTION
4H-3,1-benzoxazin-4-ones have been known for more than a century [1]. Several of these compounds have been used as linking-units in thermally stable polymer [2] and have been shown to possess biological activity. They are potent inhibitors of human leukocyte elastase [3], HSV-1 protease [4] and inactivators of Clr serine protease[5]. Moreover, 2-substituted 4H-3,1-benzoxazin-4-ones are the most frequently used precursors in the preparation of biologically active heterocyclic compounds such as quinazolinones [6]. As a result of these attractive features and in continuation of our investigation on biologically active derivatives among six-membered heterocycles [7,8].
N-(2-(4-chlorophenyl)-1-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)vinyl)-2-(1,3-dioxoisoindolin-2-yl)acetamide 2 has been synthesized by treatment of anthranilic acid with (Z)-2-((4-(4-chlorobenzylidene)-5-oxo-4,5-dihydrooxazol-2-yl)methyl)isoindoline-1,3-dione 1 in boiling butanol. The reaction of 2 with nitrogen and carbon nucleophiles and with carbon electrophiles have been investigated.
INTRODUCTION
4H-3,1-benzoxazin-4-ones have been known for more than a century [1]. Several of these compounds have been used as linking-units in thermally stable polymer [2] and have been shown to possess biological activity. They are potent inhibitors of human leukocyte elastase [3], HSV-1 protease [4] and inactivators of Clr serine protease[5]. Moreover, 2-substituted 4H-3,1-benzoxazin-4-ones are the most frequently used precursors in the preparation of biologically active heterocyclic compounds such as quinazolinones [6]. As a result of these attractive features and in continuation of our investigation on biologically active derivatives among six-membered heterocycles [7,8].