Add time:07/21/2019         Source:sciencedirect.com

A series of novel 2-aryl-6-bromo-4-chloro-8-iodoquinazolines were prepared and subjected to sequential two-step (Sonogashira and subsequent one-pot bis-Suzuki) and one-pot three-step Sonogashira cross-coupling reactions to afford unsymmetrical polycarbo-substituted quinazolines. Selectivity in the cross-coupling for these multihalogenated quinazolines was found to depend on both the intrinsic reactivity of the Csp2–halogen bond, which relates to the bond dissociation energy or bond strength and the electronic position of the halogen atom on the electron deficient scaffold (trend: Csp2–I>C(4)–Cl>Csp2–Br). The electronic absorption and emission properties of the prepared polycarbo-substituted quinazolines were evaluated in solution by means of UV–vis and emission spectroscopy in conjunction with density functional theory (DFT) method.

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