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Hamidreza Safaei

Leading speaker for catalysis conferences - Hamidreza Safaei

Title: Anthranilic acid, Chemical reagent or organocatalyst: a new and efficient method for the synthesis of quinazoline derivatives

Hamidreza Safaei

Islamic Azad University, Iran


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One of the most important classes of nitrogen heterocycles is quinazoline and its derivatives have attracted significant attention due to their diverse pharmacological activities. Among various kinds of quinazoline derivatives, 2-substituted quinazolines show important biological activities, such as, anti-inflammatory, antihypertensive and anticancer properties. as a part of my ongoing program to develop new, efficient, and environmental friendly methods for the preparation of quinazolines [1,2], here a facile, efficient, and green method for the preparation of quinazoline derivatives using antranilic acid as an organocatalyst in water under room temperature is discussed. In this work we shifted the role of antranilic acid from reactant to catalyst. Considering the chemical structure of antranilic acid that has both acid and base functional group and ability of this molecule for serving as either a lewis or Brønsted hydrogen bond donor, we were designing new duty for antranilic acid in the condensation reaction of 2-aminobenzamide with aromatic aldehydes and ketones as organocatalyst. According to Kool’s finding [3], we proposed the mechanism of the reaction on the basis of activation of starting material and stabilizing of transition states (TS1,2,3) by hydrogen donor and acceptor activities of antranilic acid. This is called bifunctional organocatalysis. As a result, excellent yields, easy work-up, use of inexpensive and commercially available organocatalyst, use of water as a green solvent, and good atom economy are the main advantages of the present method.