Deproto-metallation using a mixed lithium–zinc base and computed CH acidity of 1-aryl 1 H-benzotriazoles and 1-aryl 1 H-indazoles

E Nagaradja, F Chevallier, T Roisnel…

Index: Nagaradja, Elisabeth; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Mongin, Florence Organic and Biomolecular Chemistry, 2014 , vol. 12, # 9 p. 1475 - 1487

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Citation Number: 8

Abstract

1-Aryl-1 H-benzotriazoles and-1 H-indazoles were synthesized, and their deproto- metallation using the base prepared by mixing LiTMP with ZnCl 2· TMEDA (1/3 equiv.) was studied. In the indazole series, reactions occurring at the 3 position were followed by ring opening, and functionalization of the substrate was only found possible (on the sulfur ring) using 2-thienyl as aryl group. In the benzotriazole series, either mono-or bis-deprotonation ...

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