Synthesis of Biginelli dihydropyrimidinone derivatives with various substituents on aluminum-planted mesoporous silica catalyst
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1 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Supplementary Information for Synthesis of Biginelli dihydropyrimidinone derivatives with various substituents on aluminum-planted mesoporous silica catalyst iroaki Murata, aruro Ishitani, Masakazu Iwamoto* Chemical Resources Laboratory, Tokyo Institute of Technology, 429-R1- agatsuta, Midori-ku, Yokohama, , Japan Table of Contents 1. Analytical data of Al-planted MCM-41s S and 13 C-MR spectra of 4a-4q, 4s-4aa, and a S3-S29 Page 10 1
2 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry Analytical data of Al-planted MCM-41s Intensity (a.u.) Si/Al=237 Si/Al=73 Si/Al=44 Si/Al=3 Si/Al= dgrees 2-Theta Fig. S1. XRD of (Al-) M41s Sorption Desorption Si/Al=237 Si/Al=73 V a /cm 3 (STP) g -1 Si/Al=44 Si/Al=3 Si/Al= Relative Pressure (p/p 0 ) Fig. S2. 2 sorption and desorption isotherms of (Al-) M41s 2
3 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry and 13 C MR spectra of 4a-4q, 4s-4aa, and a Fig. S3. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-methyl-4-(4- methylphenyl)-2-oxo-, ethyl ester (4a) 4a 4a 3
4 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S4. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-methyl-2-oxo-4- phenyl-, ethyl ester (4b) 4b 4b 4
5 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-1,6-dimethyl-4-(4- methylphenyl)-2-oxo-, ethyl ester (4c) 4c 4c
6 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S6. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-methyl-4-(4- methylphenyl)-2-thioxo-, ethyl ester (4d) 4d S 4d S 6
7 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S7. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-chlorophenyl)-6- methyl-2-oxo-, ethyl ester (4e) Cl Cl 7
8 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S8. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-ethyl-4-(4- methylphenyl)-2-oxo-, ethyl ester (4f) Et 4f Et 4f 8
9 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S9. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4- methoxyphenyl)-6-propyl-2-oxo-, ethyl ester (4g) 9
10 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S10. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4- methoxyphenyl)-6-propyl-2-thioxo-, ethyl ester (4h) 4h S 4h S 10
11 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S11. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro -4-(4- methylphenyl)-2-oxo-6-propyl-, ethyl ester (4i) 4i 4i 11
12 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S12. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-1-methyl-4-(4- methylphenyl)-2-oxo-6-propyl-, ethyl ester (4j) 4j 4j 12
13 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S13. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-1,3-dimethyl-4-(4- methylphenyl)-2-oxo-6-propyl-, ethyl ester (4k) 4k 4k 13
14 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S14. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-methylphenyl)- 6-propyl-2-thioxo-, ethyl ester (4l) 4l S 4l S 14
15 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S1. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-chlorophenyl)- 2-oxo-6-propyl-, ethyl ester (4m) Cl 4m Cl 4m 1
16 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S16. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-chlorophenyl)- 6-propyl-2-thioxo-, ethyl ester (4n) Cl 4n S Cl 4n S 16
17 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S17. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-[(4- trifuluoromethyl)-phenyl]-6-propyl-2-oxo-, ethyl ester (4o) CF 3 4o CF 3 4o 17
18 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S18. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-hexyl-4-(4- methylphenyl)-2-oxo-, ethyl ester (4p) n-ex 4p n-ex 4p 18
19 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S19. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-phenyl-6-(2- phenylethyl)-2-oxo-, ethyl ester (4q) 2 C 2 C 4q 2 C 2 C 4q 19
20 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S20. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-cyclohexyl-4-(4- methylphenyl)-2-oxo-, ethyl ester (4s) c-ex 4s c-ex 4s 20
21 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S21. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-t-butyl-4-phenyl- 2-oxo-, ethyl ester (4t) t-bu 4t t-bu 4t 21
22 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S22. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-(1-heptenyl)-4-(4- methylphenyl)-2-oxo-, ethyl ester (4u) n-c 11 4u n-c 11 4u 22
23 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S23. 1 and 13 C MR spectra of -pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-6-cyclohexyl-4-(4- methylphenyl)-2-oxo-, ethyl ester (4v) n-c 11 4v n-c 11 4v 23
24 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S24. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4- methoxyphenyl)-6-phenyl-2-thioxo-, ethyl ester (4w) 4w S 4w S 24
25 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S2. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-methylphenyl)- 2-oxo-6-phenyl-, ethyl ester (4x) 4x 4x 2
26 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S26. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4-methylphenyl)- 6-phenyl-2-thioxo-, ethyl ester (4y) 4y S 4y S 26
27 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S27. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-4,6-diphenyl-, ethyl ester (4z) 4z 4z 27
28 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Fig. S28. 1 and 13 C MR spectra of -Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(4- methoxyphenyl)-6-phenyl-2-thioxo-, ethyl ester (4aa) Cl S Cl S 28
29 Supplementary Material (ESI) for rganic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2010 Figure S29. 1 and 13 C MR spectra of exanoic acid, 2-[(4-methylphenyl)methylene]-3-oxo-, ethyl ester (Ca. /4 E/Z mixture) (a) Et a Et a 29
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