A Convenient One-Pot Synthesis of Indane-1,2,3-triones by Oxidation of Indan-1-ones with N-Bromosuccinimide-dimethyl Sulfoxide Reagent

Abstract

Indane-1,2,3-triones (2a-f) have been synthesized via bromination of indan-1-ones (1a-f), followed by oxidation of the resulting brominated indan-1-ones with dimethyl sulfoxide in one pot in good yields.

Notes

For 2,2-dibromo-5-fluoroindan-1-one: pale brown solids, m.p. = 274–275 °C (decomp), IR(KBr) 1728(C=O), 1613, 1593, 1256 cm⁻¹; ¹H NMR(CDCl₃): δ, 3.49(s, 2H), 7.41–7.49(m, 2H, ArH), 7.81–7.87(m, ¹H, ArH); ¹³C NMR(DMSO-d₆): δ, 52.26, 58.56, 114.84(J=23.6 Hz), 118.66(J=23.9 Hz), 126.10(J=1.7 Hz), 128.44(J=10.9 Hz), 130.12 (J=10.9 Hz), 168.87(J=257.0 Hz), 192.39: MS (EI) m/z: 306, 308, 310 (M⁺, M⁺+2, M⁺+4, 10, 20, 10), 227, 229 (M⁺-Br, M⁺+2-Br, 80, 80), 148 (60), 120(100), 94 (30)

The intermediates 3-bromoindan-1-one, indane-1,3-dione and 2-bromo-indane-1,3-dione were detected by GC-MS analysis