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

ajha@acadiau.ca

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

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