Substituted 2-styrylquinolines Quinoline nucleus is present in many biologically active classes of compounds. Some of them are used as antiprotozoic, antibacterial and antifungal drugs [1]. Among the various classes of quinolines, 2-styryl quinolines form an important group having a wide spectrum of biological activities [2 – 8] including HIV integrase inhibition activity [9 - 15].
The general method for the synthesis of these derivatives is via condensation of 2-methylquinolines with aromatic aldehydes under basic or acidic conditions [9 – 15]. Thus, 2-methylquinolines are key intermediates in the synthesis of 2-styrylquinolines. …show more content…
al. reported that the condensation of 2-aminoarylketone (1) with alkyl substituted ketones in the presence of 1-methylimidazolium trifluoroacetate([Hmim]TFA) gave substituted 2-styrylquinolines (3) as described in Scheme 2.1. It is a combination of a Knoevenagel condensation and modified Friedlander annulation reactions …show more content…
al. reported the condensation of the given 2-methylquinoline (4) with 3, 4-dihydroxybenzaldehyde in hot acetic anhydride giving 8-substituted-3', 4’-dihydroxystyrylquinolines (5) according to a Perkin-type condensation as depicted in Scheme 2.2 [20]. (4) (5) Scheme 2.2
Zamboni et. al. reported the condensation of the 2-methylquinolines (6) with 3-hydroxybenzaldehyde in hot acetic anhydride 18 hr at 120 °C affording 2-styrylquinolines (7a) as described in scheme 2.3 [21]. The condensation of 2-methylquinolines (6) with benzaldehydes under MW irradiation in the presence of zinc chloride without a solvent giving 2-styrylquinolines (7b) was reported by Li et. al. [22] (Scheme 2.4).
(6) (7b) Scheme