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Synlett 2016; 27(20): 2807-2810
DOI: 10.1055/s-0036-1588074
DOI: 10.1055/s-0036-1588074
letter
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
Further Information
Publication History
Received: 14 July 2016
Accepted after revision: 31 August 2016
Publication Date:
19 September 2016 (online)
◊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.
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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)