Controlled Synthesis of Electron Deficient Nitro-1H-benzotriazoles

Nitro-1H-benzotriazole derivatives containing electron withdrawing substitutents in the ortho and meta positions to the nitro group have been synthesized by the simple and direct nitration of the parent 1H-benzotriazoles.The route of nitration and assignment of isomerism in these compounds is proposed based upon high level density functional theory (DFT) calculations.2][3] The synthesis of nitroaromatic derivatives containing ortho and para directed withdrawing groups is generally difficult to achieve, through the strong meta directing influence of the electron deficient groups. 4Consequently, new simple routes to the preparation of these important compounds are desirable.As part of our current studies in benzotriazole chemistry we required the use of electron deficient nitro-1H-benzotriazoles, preferably containing withdrawing groups in the ortho position to the nitro, as key building blocks towards other