Copper-Catalyzed Chelation Assisted ortho-Nitration of 2-Aryls with Pharmacophoric Benzo-thiazoles and -oxazoles as Directing Groups.

Copper-catalyzed chelation assisted ortho-nitration of aryls with benzazoles as efficient directing group has been achieved. The reaction is general and efficient for electronically differentiated aryls and pharmacophorically important directing groups i.e., benzoxazoles, benzthiazoles and benzimidazoles. This class of nitro-products have significance as fluorogenic and potential nitroreductase substrates for the detection of clinically important microorganisms. The nitration reaction proceeds with inexpensive copper catalyst and mild, cheap and environmentally friendly nitro source, Fe(NO3)3.9H2O. This operationally simple and functional group tolerant protocol highlights the high regioselectivity for the nitration of 2-aryl benzazoles without the exclusion of air or moisture.

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