Synthesis of Isoindolo[2,1-a]quinazoline, Isoindolo[2,1-a]pyrrolo [2,1-c]quinoxalinone, and Indolo[1,2-a]isoindolo[1,2-c]quinoxalinone Derivatives in a Deep Eutectic Solvent

^◊These authors contributed equally.

Abstract

2-Formylbenzoic acid reacts with various derivatives of 2-aminobenzamide, 2-(1H-pyrrol-1-yl)aniline or 2-(1H-indol-1-yl)aniline in a deep eutectic solvent to give the corresponding derivatives of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione, isoindolo[2,1-a]pyrrolo[2,1-c]quinoxalin-10(14bH)-one, and indolo[1,2-a]isoindolo[1,2-c]quinoxalin-11(15bH)-one, respectively . This protocol is operationally simple, mild, and efficient.

Key words

eutectics - formylbenzoic acid - isoindoloquinazolinediones - isoindolopyrroloquinoxalinones - indoloisoindoloquinoxalinones derivatives - aminobenzamides

• References and Notes

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• 37 6,6a-Dihydroisoindolo[2,1-a]quinazoline-5,11-diones 3a–g, Isoindolo[2,1-a]pyrrolo[2,1-c]quinoxalin-10(14bH)-ones 5a–f, and Indolo[1,2-a]isoindolo[1,2-c]quinoxalin-11(15bH)-ones 7a,b; General Procedure To a mixture of 2-formylbenzoic acid (1; 1 mmol) and the appropriate amine 2, 4, or 6 (1 mmol) was added the DES (1.5 g), prepared from ChCl and TsOH.³¹ The resulting mixture was stirred at r.t. until the starting materials were completely consumed (TLC). The reaction mass was then diluted with H₂O (5 mL), and the desired product, obtained as a precipitate, was isolated by filtration and crystallized from the appropriate solvent. The filtrate was evaporated under vacuum at 70 °C for 2 h, and the residual DES was reused in further reaction cycles. 6,6a-Dihydroisoindolo[2,1-a]quinazoline-5,11-dione (3a) White solid; yield: 237 mg (95%); ¹H NMR (500 MHz, DMSO-d ₆): δ = 9.406 (s, 1 H), 8.089 (d, J = 7.5 Hz, 1 H), 7.983 (d, J = 7 Hz, 1 H), 7.898 (d, J = 7 Hz, 2 H), 7.801 (t, J = 7 Hz, 1 H), 7.724–7.688 (m, 2 H), 7.361 (t, J = 7 Hz, 1 H), 6.526 (s, 1 H)