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Current Organic Chemistry

Author(s): Mohd. Faheem, Anjani K. Tiwari and Vinay K. Singh*

DOI: 10.2174/1385272824999200528124440

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A Review on Modern Synthetic Route for the Construction of 1, 3-Diazanaphthalene Moiety

Page: [1108 - 1138] Pages: 31

  • * (Excluding Mailing and Handling)

Abstract

Quinazoline is an organic heterocyclic molecule in which two six-membered aromatic rings are fused. Two nitrogen atoms are present in the quinazoline molecule at 1 and 3 positions that is why it is also known as 1,3-diazanaphthalene. The presence of these two nitrogen atoms in 1,3-diazanaphthalene increases the usefulness of this molecule in the field of pharmaceutical sciences. Many reactions have been reported to prepare 1,3- diazanaphthalene by aminobenzonitrile, o-aminobenzohydrazide, aminobenzamide, aminoacetophenone, and aminobenzoketone under different solvent conditions, but condensation of anthranilic acid with an aromatic aldehyde is the most common method. Later, metal-free and solvent-free conditions dominated over the old methods. This review describes the synthesis of 1,3-diazanaphthalene under different metal catalysts, reagents, solvent- free conditions and under microwave radiation through nucleophilic substitution reaction, condensation, and aromatization. In biological sciences, 1,3-diazanaphthalene derivatives have got an important place due to their ability to bind to different target sites and subsequent discovery of many drug structures.

Keywords: 1, 3-diazanaphthalene, natural alkaloid, nucleophilic substitution reaction, heterocyclic chemistry, quinazoline, quinazolinone.

Graphical Abstract

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