New Journal of Chemistry. Synthesis and mechanism of novel fluorescent coumarindihydropyrimidinone. multicomponent reaction.
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1 Electronic Supplementary Material (ESI) for ew Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre ational de la Recherche Scientifique 2015 ew Journal of Chemistry Synthesis and mechanism of novel fluorescent coumarindihydropyrimidinone dyads obtained by Biginelli multicomponent reaction. Felipe Vitório a,b, Thiago Moreira Pereira a, Rosane ora Castro b, Guilherme Pereira Guedes b, Cedric Stephan Graebin a,b and Arthur Eugen Kummerle*,a,b a Laboratório de Diversidade Molecular e Química Medicinal (LaDMol-QM, Molecular Diversity and Medicinal Chemistry Laboratory), Departament of Chemistry, Universidade Federal Rural do Rio de Janeiro, Seropédica, Rio de Janeiro, , Brazil. b Programa de Pós-Gradução em Química (PPGQ), Universidade Federal Rural do Rio de Janeiro, Seropédica, Rio de Janeiro, , Brazil. akummerle@ufrrj.br Supporting Information Contents Copies of 1, 13 CMR and Mass Spectra for all products PLC data analysis Crystal Structure analysis
2 Et Fig. S1 1 MR (500 Mz), 13 C MR (125 Mz) spectra of 3a in DMS-d6. 2
3 Et Chemical Formula: C Molecular Weight: 276,2415 Fig. S2 ESI spectra of 3a. 3
4 Et Et Et Fig. S3 1 MR (500 Mz), 13 C MR (125 Mz) spectra of 3b in DMS-d6. 4
5 Et Et Et Chemical Formula: C Molecular Weight: 331,3630 Fig. S4 ESI spectra of 3b. 5
6 Fig. S5 1 MR (400 Mz), 13 C MR (100 Mz) spectra of 4a in DMS-d6. 6
7 Chemical Formula: C Molecular Weight: 406,3881 Fig. S6 ESI spectra of 4a. 7
8 2 Fig. S7 1 MR (400 Mz), 13 C MR (100 Mz) spectra of 4b in DMS-d6. 8
9 2 Chemical Formula: C Molecular Weight: 451,3857 Fig. S8 ESI spectra of 4b. 9
10 Fig. S9 1 MR (400 Mz), 13 C MR (100 Mz) spectra of 4c in DMS-d6. 10
11 Chemical Formula: C Molecular Weight: 422,3875 Fig. S10 ESI spectra of 4c. 11
12 Fig. S11 1 MR (400 Mz), 13 C MR (100 Mz) spectra of 4d in DMS-d6. 12
13 Chemical Formula: C Molecular Weight: 436,4141 Fig. S12 ESI spectra of 4d. 13
14 Fig. S13 1 MR (500 Mz), 13 C MR (100 Mz) spectra of 4e in DMS-d6. 14
15 Chemical Formula: C Molecular Weight: 436,4141 Fig. S14 ESI spectra of 4e. 15
16 Fig. S15 1 MR (500 Mz), 13 C MR (125 Mz) spectra of 4f in DMS-d6. 16
17 Chemical Formula: C Molecular Weight: 450,3976 Fig. S16 ESI spectra of 4f. 17
18 Fig. S17 1 MR (500 Mz), 13 C MR (125 Mz) spectra of 4g in DMS-d6. 18
19 Chemical Formula: C Molecular Weight: 496,4661 Fig. S18 ESI spectra of 4g. 19
20 F Fig. S19 1 MR (500 Mz), 13C MR (125 Mz) spectra of 4h in DMS-d6. 20
21 F Chemical Formula: C F 2 6 Molecular Weight: 424,3786 Fig. S20 ESI spectra of 4h. 21
22 Cl Fig MR (400 Mz), 13 C MR (100 Mz) spectra of 4i in DMS-d6. 22
23 Cl Chemical Formula: C Cl 2 6 Molecular Weight: 440,8332 Fig. S22 ESI spectra of 4i. 23
24 Br Fig MR (500 Mz), 13 C MR (100 Mz) spectra of 4j in DMS-d6. 24
25 Br Chemical Formula: C Br 2 6 Molecular Weight: 485,2842 Fig. S24 ESI spectra of 4j. 25
26 S Fig MR (500 Mz), 13 C MR (100 Mz) spectra of 4k in DMS-d6. 26
27 S Chemical Formula: C S Molecular Weight: 412,4158 Fig. S26 ESI spectra of 4k. 27
28 S Fig. S27 1 MR (400 Mz), 13 C MR (100 Mz) spectra of 4l in DMS-d6. 28
29 S Chemical Formula: C S Molecular Weight: 413,4039 Fig. S28 ESI spectra of 4l. 29
30 Fig. S29 1 MR (400 Mz), 13 C MR (100 Mz) spectra of 4m in DMS-d6. 30
31 Chemical Formula: C Molecular Weight: 407,3762 Fig. S30 ESI spectra of 4m. 31
32 Br Fig. S31 1 MR (500 Mz), 13 C MR (125 Mz) spectra of 4n in DMS-d6. 32
33 Br Chemical Formula: C 21 16Br 3 6 Molecular Weight: 486,2722 Fig. S32 ESI spectra of 4n. 33
34 S Fig. S33 1 MR (500 Mz), 13 C MR (125 Mz) spectra of 4o in DMS-d6. 34
35 Chemical Formula: C S Molecular Weight: 422,4537 S Fig. S34 ESI spectra of 4o. 35
36 Fig. S35 1 MR (500 Mz), 13 C MR (125 Mz) spectra of 4p in DMS-d6. 36
37 Chemical Formula: C Molecular Weight: 461,5097 Fig. S36 ESI spectra of 4p. 37
38 Fig. S37 1 MR (500 Mz), 13 C MR (125 Mz) spectra of 4q in DMS-d6. 38
39 Chemical Formula: C Molecular Weight: 491,5357 Fig. S38 ESI spectra of 4q. 39
40 Cl Fig. S39 1 MR (500 Mz), 13 C MR (125 Mz) spectra of 4r in DMS-d6. 40
41 Cl Chemical Formula: C Cl 3 5 Molecular Weight: 495,9547 Fig. S40 ESI spectra of 4r. 41
42 Et Fig. S41 1 MR (500 Mz), 13 C MR(125 Mz) spectra of 5 in DMS-d6. 42
43 Et Chemical Formula: C Molecular Weight: 364,3481 Fig. S42 ESI spectra of 5. 43
44 PLC data analysis A B C D Fig. S43 Comparison of reaction catalyzed conditions. A 2 S 4 (25 µl); B 2 S 4 (12.5 µl); C Cl (25 µl); D Cl (12.5 µl). nd not determined product. 44
45 A B C D Fig. S44 Reaction conditions: non-catalyzed. A 2 hours time reaction; B 4 hours time reaction; C 10 hours time reaction and D 24 hours time reaction; nd not determinate. 45
46 A B C D Fig. S45 Reaction conditions: acetic acid as catalyst. A 2 hours time reaction; B 4 hours time reaction; C 10 hours time reaction and D 24 hours time reaction; nd not determinated. 46
47 A B C D Fig. S46 Reaction conditions: Lewis acid as catalyst (CaF 2 ): A 2 hours time reaction; B 4 hours time reaction; C 10 hours time reaction and D 24 hours time reaction; nd not determinated. 47
48 A B C D Fig. S47 Reaction conditions: Cl as catalyst (12.5µL): A 2 hours time reaction; B 4 hours time reaction; C 10 hours time reaction and D 24 hours time reaction; nd not determinated. 48
49 X-ray diffraction Single crystal X-ray diffraction data for compound 4c were collected on an Bruker D8 Venture diffractometer at room temperature, using graphite monochromatic MoKα radiation (λ = Å). Data collection and cell refinement were performed with Bruker Instrument Service v4.2.2 and APEX2 [ i ], respectively. Data reduction was carried out using SAIT [ ii ]. Empirical multiscan absorption correction using equivalent reflections was performed with the SADABS program [ iii ]. The structure solutions and full-matrix least-squares refinements based on F 2 were performed with the SELXS-97 and SELXL-97 program packages [iv]. All atoms except hydrogen were refined anisotropically. ydrogen atoms were treated by a mixture of independent and constrained refinement. The structure was drawn by Mercury program [v]. Details of data collection and refinement are listed in Table S1. Table S1: Summary of crystal data and structure refinement of compound 4c. Empirical formula C Formula weight Temperature 293(2) K Wavelength Å Crystal system Triclinic Space group P -1 Unit cell dimensions a = (5) Å α= (2) b = (6) Å β= (2) c = (6) Å γ = (2) Volume (10) Å 3 Z Density (calculated) Absorption coefficient Mg/m mm -1 F(000) Crystal size x 0.17 x 0.05 mm 3 49
50 Theta range for data collection 2.1 to 25.0 Index ranges -10<=h<=10, -12<=k<=12, -15<=l<=15 Reflections collected Independent reflections 4053 [R(int) = 0.075] Completeness to theta = % Max. and min. transmission Refinement method and Full-matrix least-squares on F 2 Data / restraints / parameters Goodness-of-fit on F / 0 / Final R indices [I>2sigma(I)] R 1 = 0.062, wr 2 = R indices (all data) Largest diff. peak and hole R 1 = 0.099, wr 2 = and e.å -3 Fig. S48 Molecular structure of compound 4c. Thermal ellipsoids are drawn at 40 % of probability. Crystallization solvent molecule was omitted for sake of clarity. [ i ] Bruker (2007). APEX2 v Bruker AXS Inc., Madison, Wisconsin, USA. [ ii ] Bruker (2013). SAIT v8.34a. Bruker AXS Inc., Madison, Wisconsin, USA. [ iii ] Sheldrick, G.M. SADABS, Program for Empirical Absorption Correction of Area Detector Data, University of Göttingen, Germany, [ iv ] Sheldrick, G.M. Acta Cryst. 2008, A64,
51 [ v ]Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J., J. Appl. Cryst. 2006, 39,
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