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Synlett 2015; 26(18): 2575-2577
DOI: 10.1055/s-0035-1560483
DOI: 10.1055/s-0035-1560483
letter
Efficient Access to 2,3-Dihydroquinazolin-4(1H)-ones by Environmentally Benign l-Proline Nitrate as Recyclable Catalyst
Further Information
Publication History
Received: 10 July 2015
Accepted after revision: 24 August 2015
Publication Date:
15 September 2015 (online)
Abstract
An l-proline nitrate assisted protocol is described for the construction of 2,3-dihydroquinazolin-4(1H)-ones. The catalyst can be recovered easily and is reusable for at least six cycles without significant loss of catalytic efficiency.
Key words
2,3-dihydroquinazolin-4(1H)-one - l-proline nitrate - ionic liquid - cyclocondensation reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560483.
- Supporting Information
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References and Notes
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- 20 General Procedure A mixture of anthranilamide (1.46 mmol), aldehyde (1.46 mmol), and l-proline nitrate (10 mol%) was stirred at r.t. in MeCN (0.5 mL). The progress of the reaction was monitored by TLC. After completion of reaction, the solid obtained was filtered and recrystallized from EtOH to give 3a–o. To recover the catalyst, the filtrate was evaporated under reduced pressure. The residue obtained was washed with a small quantity of H2O. This was again removed under reduced pressure, and the last traces of H2O were removed azeotropically with a small volume of toluene to obtain the catalyst in a suitable form for the next reaction.
- 21 Representative Characterization Data Compound 3g: white solid; yield 87%; mp 168–170 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 8.24 (s, 1 H, NH), 7.07 (s, 1 H, NH), 7.62 (d, J = 7.6 Hz, 1 H, Ar), 7.34 (d, J = 7.6 Hz, 1 H, Ar), 7.13 (d, J = 6.2 Hz, 1 H, Ar), 6.86–6.65 (m, 5 H, 1 NH, 4 Ar), 6.00 (s, 1 H), 2.88 (sept, J = 7.2 Hz, 1 H, CH(CH3)2), 1.17 [d, J = 7.2Hz, 6 H, CH(CH3)2].
- 22 Compound 3k: white solid; yield 87%; mp 210–211 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 9.86 (s, 1 H, OH), 7.94 (s, 1 H, NH), 6.95 (s, 1 H, NH), 7.62 (d, J = 7.6 Hz, 1 H, Ar), 7.34 (d, J = 7.6 Hz, 1 H, Ar), 7.13 (d, J = 6.2 Hz, 1 H, Ar), 6.86–6.65 (m, 5 H, 1 NH, 4 Ar), 6.00 (s, 1 H).
- 23 Compound 3l: white solid; yield 90%; mp 208–210 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 9.12 (s, 1 H, OH), 7.69 (s, 1 H, NH), 6.29 (s, 1 H, NH), 7.68 (d, J = 7.64 Hz, 1 H, Ar), 7.23–6.64 (m, 8 H, Ar), 5.66 (s, 1 H).
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For chiral phosphoric acid, see:
For TFA, see:
For p-TsOH, see:
For gallium triflate, see:
For silica-H2SO4, see:
For calix[4]arene (p-SAC), see:
For MNP-PSA (N-propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles), see:
For Cu-CNTs, see:
For low-valent titanium reagents, see:
For β-cyclodextrin, see:
For [bmim]PF6, see:
For TBAB, see: