Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M....
Transcript of Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M....
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Supporting Information
Transition metal-free one-pot cascade synthesis of 7-oxa-2-azatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-3-ones from biomass-
derived levulinic acid under mild conditions Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik
Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6, Canada
Table of Contents for Supporting Information
1. 1H and 13C NMR spectra of 1a-1i S2 2. 1H and 13C NMR spectra of 1a’-1i’ S11 3. 1H and 13C NMR spectra of 2a, 2b, 2c, 3a and 3b S20
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1H and 13C NMR spectra of 1a-1i
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N
O
O
I
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1H and 13C NMR spectra of 1a’-1i’
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1H and 13C NMR spectra of 2a, 2b, 2c, 3a and 3b
1.0001.1412.3421.1611.0641.992 1.0611.025 3.089
PPM 8.8 8.4 8.0 7.6 7.2 6.8 6.4 6.0 5.6 5.2 4.8 4.4 4.0 3.6 3.2 2.8 2.4 2.0 1.6 1.2 0.8 0.4 0.0
8.15658.14067.82877.82737.81377.69517.68147.66647.65437.65227.64937.64267.64137.62877.62767.62617.58117.57837.56607.56377.55217.54937.34177.33447.32947.32597.31877.31317.15857.15657.14617.1448 5.38205.37925.20345.17224.96284.9316 1.71951.7168
PPM 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20
19.651961.949886.9751120.1456121.0554121.9466122.8464123.2400123.4008126.5018129.0887129.8921131.4060132.1679145.0036163.7866
N
O
O
N
O
O
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NH
OH
O4
O
NH
OH
O4
O
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1.0000.976 1.1471.0611.008 2.152 2.1892.4023.082 2.3282.6702.3710.808
PPM 8.4 8.0 7.6 7.2 6.8 6.4 6.0 5.6 5.2 4.8 4.4 4.0 3.6 3.2 2.8 2.4 2.0 1.6 1.2 0.8
8.7014 8.07318.05697.36497.36207.34917.34717.33397.33097.29917.22147.20677.11977.1050 4.7227 2.50112.48662.47222.43462.41982.40502.16652.14551.78021.76501.74991.66311.64791.63261.61791.42861.41961.41381.40241.3979
PPM 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20
23.475325.529128.769730.192937.732043.602264.6300122.7085124.4659129.0690129.2580129.8256137.6608171.9134209.6897
NH
OH
O5
O
NH
OH
O5
O
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013