Copper-Catalyzed Domino Reaction of 2-Haloanilines with Hydrazides: A New Route for the Synthesis of Benzo[e][1,2,4]triazine Derivatives

Abstract

A copper-catalyzed domino reaction for the synthesis of benzo[e][1,2,4]triazine derivatives has been developed using readily available substituted 2-haloanilines and hydrazides as the starting materials. The procedure of the present method is mild, facile, and efficient.

benzo[e][1,2,4]triazine derivatives - 2-haloanilines - ­hydrazides - copper catalyst - domino reaction

References and Notes

<A NAME="RW73811ST-1">1</A>

These authors contributed equally to this work.

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Typical Procedure for the Synthesis of Benzo[ e ][1,2,4]triazine An oven-dried Schlenk tube was charged with Cu₂O (2.9 mg, 0.02 mmol), Cs₂CO₃ (130.4 mg, 0.4 mmol), 1a (44 mg, 0.20 mmol) and 2a (41 mg, 0.3 mmol). The Schlenk tube was sealed, evacuated, and backfilled with nitrogen (3 cycles). Then DMF (0.5 mL) and 1,4-dioxane (0.5 mL) were added to the reaction tube. The reaction was stirred at 90 ˚C under N₂ for 6 h. After cooling to r.t. the solvent was diluted with EtOAc (3 × 10 mL), washed with brine (3 × 10 mL), and dried over anhyd Na₂SO₄. After the solvent was evaporated in vacuo, the residues were purified by column chromatography, eluting with PE-EtOAc (20:1) to afford 31 mg (75%) of 3-phenylbenzo[e][1,2,4]triazine (3aa) as a yellow solid, mp 119-121 ˚C. ^¹H NMR (400 MHz, CDCl₃): δ = 8.77-8.74 (m, 2 H), 8.51 (dd, J = 8.4, 0.8 Hz, 1 H), 8.07 (d, J = 8.8 Hz, 1 H), 7.96-7.92 (m, 1 H), 7.83-7.78 (m, 1 H), 7.59-7.57 (m, 3 H). ^¹³C NMR (100 MHz, CDCl₃): δ = 160.0, 146.6, 141.2, 135.8, 135.6, 131.6, 130.3, 129.7, 129.3, 129.1, 128.9. IR (neat): 3368, 3060, 1506, 1329, 1016, 771, 699 cm^-¹. HRMS: m/z calcd for C₁₃H₁₀N₃ [M + H]⁺: 208.0870; found: 208.0871.

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