Rapid Cascade Synthesis of Poly-Heterocyclic Architectures from Indigo

Transcription

1 S1 Rapid Cascade Synthesis of Poly-Heterocyclic Architectures from Indigo Alireza Shakoori 1, John B. Bremner 1, Anthony C. Willis 2, Rachada Haritakun 3 and Paul A. Keller 1 * 1 School of Chemistry, University of Wollongong, Wollongong, NSW, 2522, Australia 2 School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia 3 National Centre for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), 113 Paholyothin Road, Klong 1, Klong Laung, Pahmanthani Thailand Supporting Information Table of Contents Selected NMR Spectra of Compounds S2 Selected UV-Vis. Spectra of Compounds S13 ORTEP Plots for the Three X-ray Structures Reported in this Manuscript (larger scale)...s15 Figure S1 and S2...S16 Figure S3...S17 Supplementary Pictures and Figures...S18 Figure S4: The Fluorescence Emission of Compounds 7 and 8.. S18 Figure S5:Computational Modeling for Compound 5 with Spartan 10, Geometry Optimised. S19

2 Selected NMR Spectra of Compound 4-8 S2

3 S3

4 S4

5 S5

6 S6

7 S7

8 S8

9 S9

10 S10

11 S11

12 S12

13 Selected UV-Vis. Spectra of Compound 4-7 S13

14 S14

15 S15 Ortep Plots for the Three X-ray Structures Reported in this Manuscript (larger scale) Crystallographic Studies Crystallographic Data for Compounds 6, 7 and 8 Compound 6: C 25 H 16 N 2 O 2, M = , T = 200 K, monoclinic, space group P2 1 /n, Z = 4, a = (2), b = (3), c = (4) Å, β = (15) ; V = (8) Å 3, D x = g cm 3, 4284 unique data (2θ max = 50 ), R = [for 3584 reflections with I > 2.0σ(I)]; Rw = (all data), S = Compound 7: C 25 H 16 N 2 O 2, M = , T = 200 K, monoclinic, space group P2 1 /n, Z = 4, a = (2), b = (3), c = (4) Å, β = (9) ; V = (7) Å 3, D x = g cm 3, 4287 unique data (2θ max = 50 ), R = [for 3143 reflections with I > 2.0σ(I)]; Rw = (all data), S = Compound 8: C 29 H 18 N 2 O 2, M = , T = 200 K, triclinic, space group P-1, Z = 2, a = (2), b = (3), c = (4) Å, α = (14), β = (18), γ = (19) ; V = (6) Å 3, D x = g cm 3, 5070 unique data (2θ max = 50 ), R = [for 4074 reflections with I > 2.0σ(I)]; Rw = (all data), S = Structure Determination Images were measured on a Nonius Kappa CCD diffractometer (MoKa, graphite monochromator, λ = Å) and data extracted using the DENZO package. 1 Structure solution was by direct methods (SIR92). 2 The structures of compounds 6, 7 and 8 were refined using the CRYSTALS program package. 3 Atomic coordinates, bond lengths and angles, and displacement parameters for compounds 6, 7 and 8 have been deposited at the Cambridge Crystallographic Data Centre (CCDC nos , and , respectively). These data can be obtained free-of-charge via by ing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax:

16 S16 Figure S1: Structure of compound 6 with labeling of selected atoms. Anisotropic displacement ellipsoids show 30% probability levels. Hydrogen atoms are drawn as circles with small radii. Figure S2: Structure of compound 7 with labeling of selected atoms. Anisotropic displacement ellipsoids show 30% probability levels. Hydrogen atoms are drawn as circles with small radii.

17 S17 Figure S3: Structure of compound 8 with labeling of selected atoms. Anisotropic displacement ellipsoids show 30% probability levels. Hydrogen atoms are drawn as circles with small radii.

18 S18 Supplementary Pictures and Figures Figure S4: Colour of the solutions of 7 and 8 in EtOAc under visible & UV-light and the fluorescence emission.

19 S19 Figure S5: Modeling for the position of the hydrogen atoms of the endo cyclic methylene and the exocyclic methylene in 5 with Spartan 10, Geometry Optimised, 6-31G (D) Level. References 1. DENZO SMN. Otwinowski, Z.; Minor, W. Processing of X-ray diffraction data collected in oscillation mode. In Methods in Enzymology, Volume 276: Macromolecular Crystallography, Part A; Carter Jr., C. W.; Sweet, R. M., Eds.; Academic Press: New York, 1997; pp SIR92. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, K.; Watkin, D. J. J. Appl. Crystallogr. 2003, 36, 1487.