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Synthesis and Biological Activities of Some Condensed Oxazine and Pyrimidine Derivatives: Cyclization, Ring Transformation and Functionalization of Oxazine


Affiliations
1 Department of Chemistry,Islamic University in Almadinah Almonawara, Almadinah Almonawara, Egypt
2 Department of Chemistry, Zagazig University, Zagazig 44511, Egypt
 

2-Amino benzoic acid was acylated using chloroacetyl chloride followed by cycloaddition with benzylidene derivative to yield pyrimidine 3. Benzoxazone 4 reacted with nucleophilic carbon of phenols 5 and 6, active methylene compounds 11 and 12, and enaminic carbons of 16 and 17 to yield compounds 7, 10, 13, 14, 18 and 19 respectively. Also, benzoxazone 6 reacted with hydrazine to yield compounds 5 and 33. Aminoquinazoline 5 underwent a series of reactions using benzaldhyde, NH4SCN in base/acid medium, chloroacetyl chloride and CS2 followed by cyclization using ethyl chloroacetate to yield compounds 22, 26, 29, 32, 30 and 31 respectively. Hydrazide 33 underwent a series of cycloaddition and cyclocondensation reactions using compounds like ethyl chloroacetate and/or acetyl acetone, maleic anhydride and p-chlorocinnamoyl isothiocyanate to yield compounds 34, 36, 37 and 40 respectively. Finally, compound 6 was reacted with ethyl cyanoacetate and/or acetyl acetone to form compounds 43 and 44 respectively.

Keywords

Condensed Oxazine, Cyclization, Functionalization, Pyrimidine Derivatives, Ring Transformation.
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  • Synthesis and Biological Activities of Some Condensed Oxazine and Pyrimidine Derivatives: Cyclization, Ring Transformation and Functionalization of Oxazine

Abstract Views: 371  |  PDF Views: 113

Authors

Reda A. Haggam
Department of Chemistry,Islamic University in Almadinah Almonawara, Almadinah Almonawara, Egypt
Essam Abdelghani Soylem
Department of Chemistry, Zagazig University, Zagazig 44511, Egypt
Mohammed Gomaa Assy
Department of Chemistry, Zagazig University, Zagazig 44511, Egypt
Mariam Fikery Arastiedy
Department of Chemistry, Zagazig University, Zagazig 44511, Egypt

Abstract


2-Amino benzoic acid was acylated using chloroacetyl chloride followed by cycloaddition with benzylidene derivative to yield pyrimidine 3. Benzoxazone 4 reacted with nucleophilic carbon of phenols 5 and 6, active methylene compounds 11 and 12, and enaminic carbons of 16 and 17 to yield compounds 7, 10, 13, 14, 18 and 19 respectively. Also, benzoxazone 6 reacted with hydrazine to yield compounds 5 and 33. Aminoquinazoline 5 underwent a series of reactions using benzaldhyde, NH4SCN in base/acid medium, chloroacetyl chloride and CS2 followed by cyclization using ethyl chloroacetate to yield compounds 22, 26, 29, 32, 30 and 31 respectively. Hydrazide 33 underwent a series of cycloaddition and cyclocondensation reactions using compounds like ethyl chloroacetate and/or acetyl acetone, maleic anhydride and p-chlorocinnamoyl isothiocyanate to yield compounds 34, 36, 37 and 40 respectively. Finally, compound 6 was reacted with ethyl cyanoacetate and/or acetyl acetone to form compounds 43 and 44 respectively.

Keywords


Condensed Oxazine, Cyclization, Functionalization, Pyrimidine Derivatives, Ring Transformation.

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DOI: https://doi.org/10.18520/cs%2Fv115%2Fi10%2F1893-1903