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- Ξάνθη Κούνδουρος
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1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Electronic Supplementary Information DMSO/I 2 mediated C C bond cleavage of α-ketoaldehydes followed by C O bond formation: A metal-free approach for one-pot esterification Vunnam Venkateswarlu, a,c K. A. Aravinda Kumar, a Sorav Gupta, a,c Deepika Singh, b,c Ram A. Vishwakarma, a,c Sanghapal D. Sawant a,c a Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu-80 00, India b QC-QA Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu-80 00, India c Academy of Scientific and Innovative Research, Anusandhan Bhawan, 2 Rafi Marg, New Delhi-0 00, India. sdsawant@iiim.res.in, sawant.rrl@gmail.com Tel: ; Fax: IIIM communication No.: IIIM/78/205
2 MS mass peaks of intermediates and product.0. Example for formation of carboxylic acid product : Figure showing ESI-MS and GC- Fig. S [A] The ESI-MS analysis of reaction mixture for (b), collected during progress of reaction at an interval of four hour showing the mass peaks of intermediates predicted as per plausible mechanism; [B] reaction mixture after 6 hr, shows completion of reaction; [C] GC- MS of crude sample of b, showing (MS peak A) for product 2b, and (MS peak 2A) for the fragment formed during the reaction. [D] and [E] The fragmentation pattern obtained for product and/or intermediate in GC-MS analysis 2
3 2.0. Analytical data: Benzoic acid (2a) a,b : (400 MHz, MeOD): δ 8.03 (d, J = 7.6 Hz, 2H), 7.54 (t, J = 7.3 Hz, H), 7.43 (t, J = 7.6 Hz, 2H). 3 (0 MHz, MeOD): δ 70., 34., 3.8, 30.8, (+) ESI-MS: 45. (M + + Na). 2-Bromobenzoic acid (2b) a : (400 MHz, MeOD) δ (m, H), 7.58 (d, J = 8.0 Hz, H), (m, 2H). 3 (26 MHz, MeOD) δ 69.6, 35.3, 34.5, 33.6, 32., 28.4, (-) ESI-MS: 99.2 (M + -). 4-Bromobenzoic acid (2c) a,b,d : (400 MHz, MeOD) δ 7.82 (d, J = 8.5 Hz, 2H), 7.55 (d, J = 8.5 Hz, 2H). 3 (26 MHz, MeOD) δ 68.8, 32.8, 32.5, 3., 28.8; (-) ESI-MS: 99.2 (M + -). 3-Nitrobenzoic acid (2d) a : (400 MHz, MeOD) δ 8.65 (d, J =.7 Hz, H), (m, H), 8.26 (d, J = 7.7 Hz, H), 7.63 (t, J = 8.0 Hz, H). 3 (26 MHz, MeOD) δ 65.9, 48.2, 35.0, 32.4, 29.6, 26.8, (-) ESI-MS: 66. (M + -). 3-bromo-4-fluorobenzoic acid (2e) e : (400 MHz, CDCl 3 ): δ 8.34 (m, H), 8.07 (m, H), 7.23 (m, H). 9 F NMR (376 MHz, CDCl 3 ) δ -98. (td, J = 7.2, 5.2 Hz). 3 (0 MHz, CDCl3): δ 70.2, 62.7 (d, J = Hz), 36. (d, J =.7 Hz), 3.5 (d, J = 8.8 Hz), 26.7 (d, J = 3.5 Hz), 6.7 (d, J = 23. Hz), 09.5 (d, J = 2.8 Hz); (-) ESI-MS: 26.8 (M + -). 2,4-dichlorobenzoic acid (2f) b : (400 MHz, CDCl 3 ) δ 7.99 (d, J = 8.5 Hz, H), 7.53 (d, J =.9 Hz, H), 7.35 (dd, J = 8.5, 2.0 Hz, H). 3 (0 MHz, CDCl 3 ) δ 69.2, 39.5, 36.0, 33.5, 3.4, 27.. (-) ESI-MS: 89.2 (M + -). 4-Chlorobenzoic acid (2g) b,d : (400 MHz, MeOD) δ 7.89 (d, J = 8.6 Hz, 2H), 7.38 (d, J = 8.6 Hz, 2H). 3 (0 MHz, MeOD) δ 68.7, 40.2, 32.3, (-) ESI-MS: 55.2 (M + -) 3-Bromo-4-methoxybenzoic acid (2h) c : (400 MHz, MeOD) δ 8.05 (d, J = 2. Hz, H), 7.90 (dd, J = 8.6, 2. Hz, H), 7.0 (d, J = 8.7 Hz, H), 3.85 (s, 3H). 3 (26 MHz, MeOD): δ 68.4, 6.0, 35.7, 32.0, 25.4, 2.5, 2., 57.0; (-) ESI-MS: (M + -). 3,4-Dimethylbenzoic acid (2i) d : (400 MHz, CDCl 3 ) δ (m, 2H), (m, H), 2.33 (d, J = 4.5 Hz, 6H). 3 (0 MHz, CDCl 3 ) δ 72.7, 43.3, 36.8, 3.2, 29.8, 27.8, 26.9, 20., 9.67; (-) ESI-MS: 48.8 (M + -). 3
4 4-Fluorobenzoic acid (2j) d : (400 MHz, CDCl 3 ) δ (m, 2H), 7.5 (t, J = 8.0 Hz, 2H). 3 (25 MHz, CDCl 3 ) δ 68.7, 68.4, 65.9, 38.5, 33.4, 28.4, 6.5; (-) ESI- MS: 39.0 (M + -). 4-Nitirobenzoic acid (2k) a,b : (400 MHz, MeOD) δ 8.23 (d, J = 8.8 Hz, 2H), 8.3 (d, J = 8.8 Hz, 2H). 3 (26 MHz, MeOD) δ 67.6, 5.9, 37.6, 3.9, (-) ESI-MS: 66.2 (M + -). 4-Methylbenzoic acid (2l) a,b : (400 MHz, CDCl 3 ) δ 8.03 (d, J = 8. Hz, 2H), 7.27 (t, J = 8. Hz, 2H), 2.46 (s, 3H). 3 (0 MHz, MeOD) δ 70.0, 45.0, 30.8, 30., 29., 2.6; (+) ESI-MS: 37.4 (M + + ). 4-Phenylbenzoic acid (2m) d : (500 MHz, MeOD) δ 7.99 (dt, J = 8.4,.8 Hz, 2H), (m, 2H), (m, 2H), (m, 2H), (m, H). 3 (26 MHz, MeOD) δ 69.7, 47.0, 4.2, 3.3, 30.6, 30.0, 29.2, 28.2, (-) ESI-MS: 97.3 (M + -). 3,4,5-Trimethoxybenzoic acid (2n) e : (400 MHz, CDCl 3 ) δ 7.38 (s, 2H), 3.94 (s, 3H), 3.93 (s, 6H). 3 (26 MHz, CDCl 3 ) δ 7.4, 52.9, 42.9, 24., 07.3, 60.9, (-) ESI-MS: 2.2 (M + -). 4-methoxybenzoic acid (2o) a,b : (500 MHz, MeOD) δ 7.87 (d, J = 8.9 Hz, 2H), 6.87 (d, J = 8.9 Hz, 2H), 3.75 (s, 3H). 3 (26 MHz, MeOD): δ69.8, 65.0, 32.8, 24.0, 4.6, (-) ESI-MS: 5.2(M + -) 4-methoxy-2-methylbenzoic acid (2p) c : (400 MHz, DMSO-d 6 ) δ 7.84 (d, J=8.3Hz, H), 6.84 (s,h), 6.82 (s, H), 3.79 (s, 3H), 2.52 (s, 3H). 3 CMR (26MHz, DMSO-d 6 ) δ 68.0, 6.7, 42., 32.7, 22.0, 6.6,., 55.2, 2.8, (+) ESI-MS: 63.3 (M + +). 4-(tert-butyl)benzoic acid a (2q): (400 MHz, CDCl 3 ): δ 8.04 (d, J = 8.5 Hz, 2H), 7.49 (d, J = 8.5 Hz, 2H),.35 (s, 9H). 3 (26 MHz, CDCl 3 ): δ 72.4, 50.2, 30., 29., 25.6, 40.6, 3.3. (-) ESI-MS: 77.2 (M + -). 4-bromo-3-chlorobenzoic acid l (2r): (400 MHz, CDCl 3 ): δ (t, H), (m, H), (d, J = 4 Hz, H). 3 (26 MHz, CDCl 3 ): δ 67.4, 36.5, 34.9, 34.0, 33.7, 33.5, 2.. (-) ESI-MS: (M + -). 3-chlorobenzoicacid b (2s): (400 MHz, CDCl 3 ): δ 8.09 (s, H), 8.00 (d, J = 7.7 Hz, H), 7.59 (d, J = 8.0 Hz, H), 7.42 (t, J = 7.9 Hz, H). 3 (0 MHz, MeOD): δ 68.4, 35.5, 33.9, 3.2, 30.5,
5 Nicotinic acid g (3a) : (400 MHz, MeOD) δ 9.02 (s, H), 8.64 (d, J = 3.6 Hz, H), 8.32 (dt, J = 7.9,.8 Hz, H), 7.48 (dd, J = 7.7, 5. Hz, H); 3 (0 MHz, MeOD) δ 67.7, 53.6, 5.2, 39.3, 28.7, (+) ESI-MS: 24.2 (M + +). 5-methylthiophene-2-carboxylic acid h (3b): (500 MHz, CDCl 3 ) δ 7.7 (d, J = 2.6 Hz, H), 6.8 (s, H), 2.55 (s, 3H). 3 (26 MHz, CDCl 3 ) δ 65.6, 47.7, 33.4, 28.0, 24.6, 3.7. (+) ESI-MS: 43. (M + +). 4-Phenoxybenzoic acid c (3c): (400 MHz, CDCl3): δ 8.08 (d, J = 8.8 Hz, 2H),.4 (t, J = 7.9 Hz, 2H), 7.2 (t, J = 7.4 Hz, H), 7.09 (d, J = 7.7 Hz, 2H), 7.0 (d, J = 8.8 Hz, 2H). 3 C NMR (26 MHz, MeOD): δ 69.3, 63.4, 57.09, 33.0, 3.2, 26., 25.7, 2.2, 8.2. Benzofuran-2carboxylic acid c (3d): (500 MHz, MeOD): δ 7.72 (d, J = 7.9 Hz, H), 7.57 (t, J = 4.2 Hz, 2H), (m, H), 7.3 (t, J = 7.5 Hz, H). 3 (26 MHz, MeOD): δ 6.0, 55.7, 46.0, 27.3, 27., 23.5, 22.6, 3.4,.5. ESI-MS: 63.2 (M + +H). 2-Furaic acid j (3e): (500 MHz, CDCl 3 ): δ 0.92 (s, H), 7.65 (d, J = 2. Hz, H), 7.34 (dd, J = 22.5, 3.4 Hz, H), (m, H). 3 (26 MHz, CDCl 3 ): δ 63.8, 47.5, 43.8, 20.2, 2.3. (+) ESI-MS: 3.2 (M + +). Methyl benzoate 2a (4a): (400 MHz, CDCl 3 ) δ (m, 2H), 7.67 (t, J = 7.4 Hz, H), 7.52 (t, J = 7.8 Hz, 2H), 3.99 (s, 3H); GC-MS:36. (M + ). Methyl 4-methoxybenzoate 2a (4b): (400 MHz, CDCl 3 + CD 3 OD) δ 8.00 (d, J = 8.7 Hz, 2H), 6.92 (d, J = 8.8 Hz, 2H), 3.89 (s, 3H), 3.86 (s, 3H). Methyl 2-fluorobenzoate 2b (4c): (400 MHz, CDCl 3 ) δ 7.94 (td, J = 7.6,.8 Hz, H), (m, H), (m, 2H), 3.93 (s, 3H); GC-MS:54.0 (M + ). Methyl 4-aminobenzoate 2a (4d): (400 MHz, CDCl 3 ) δ 7.84 (d, J = 8.6 Hz, 2H), 6.62 (d, J = 8.6 Hz, 2H), 4.5 (s, 2H), 3.84 (s, 3H); GC-MS:5. (M + ). 3 (26 MHz, CDCl 3 ): δ 67.28, 5.02, 3.6, 9.52, 3.79, Methyl 5-methylthiophene-2-carboxylate 2c (4e): (400 MHz, CDCl 3 ) δ 7.6 (d, J = 3.7 Hz, H), 6.76 (dd, J = 3.7, 0.9 Hz, H), 3.86 (s, 3H), 2.52 (s, 3H). Ethyl benzofuran-2-carboxylate 2d (4f): (400 MHz, CDCl 3 ) δ 7.67 (d, J = 7.9 Hz, H), 7.59 (d, J = 8.4 Hz, H), 7.52 (s, H), (m, H), 7.29 (dd, J = 3.2, 6.0 Hz, H), 4.44 (q, J = 7. Hz, 2H),.42 (t, J = 7. Hz, 3H). 5
6 Dihydro β-ionic Acid 2e (5a): (400 MHz, CDCl 3 ): δ (m, 2H), (m, 2H), (t, J = 6.2 Hz, 2H),.6 (s, 3H),.6.55 (m, 2H),.44.4 (m, 2H),.00 (s, 6H). 3 (0 MHz, CDCl 3 ): δ 80.3, 35.4, 28.5, 39.7, 34.9, 34.7, 32.7, 28.3, 23.5, 9.65, 9.4. HRMS (+ESI, m/z) calc for C 2 H 20 O 2 (M + ) , found (M+H + )
7 2.0. Scanned Spectra Benzoic Acid (2a): 3 7
8 2-Bromobenzoic acid (2b): 3 8
9 4-Bromobenzoic acid (2c): 3 9
10 3-Nitrobenzoic acid (2d): 3 0
11 3-bromo,4-Fluorobenzoic acid (2e): 9 F NMR
12 3 2
13 2,4-dichloro benzoic acid (2f): 3 3
14 4-Chloro benzoic acid (2g): 3 4
15 3-Bromo,4-methoxy benzoic acid (2h): 3 5
16 3,4-Dimethylbenzoic acid (2i): O OH 3 O OH 6
17 4-Fluorobenzoic acid (2j): 3 7
18 4-Nitiro benzoic acid (2k): 3 8
19 4-Methyl benzoic acid (2l): 3 9
20 4-Phenyl Benzoic acid (2m): 3 20
21 3,4,5 Trimethoxybenzoic acid (2n): 3 2
22 4-methoxybenzoic acid (2o): 3 22
23 4-methoxy-2-methylbenzoic acid (2p): 3 23
24 4-(tert-butyl)benzoic acid (2q): f (ppm) f (ppm)
25 25 4-bromo-3-chlorobenzoic acid (2r): HNMR: f (ppm) f (ppm) : f (ppm)
26 3-Chlorobenzoic acid (2s): f (ppm) f (ppm) f (ppm)
27 Nicotinic acid (3a): 3 27
28 5-methylthiophene-2-carboxylic acid (3b): f (ppm) f (ppm)
29 4-Phenoxybenzoic acid (3c): 3 29
30 30 Benzofuran-2-carboxylic acid (3d): f (ppm) f (ppm) f (ppm)
31 2-Furaic acid (3e): f (ppm) f (ppm)
32 Methyl benzoate (4a): 32
33 Methyl 4-methoxybenzoate (4b): 33
34 Methyl 2-fluorobenzoate (4c): 34
35 Methyl 4-aminobenzoate (4d): f (ppm)
36 Methyl 5-methylthiophene-2-carboxylate (4e): 36
37 Ethyl benzofuran-2-carboxylate (4f): O O O 37
38 Dihydro β-ionic Acid (5a): f (ppm) f (ppm)
39 HRMS 39
40 References. (a) T. M. Shaikh and F. -E. Hong, Adv. Synth. Cat., 20, 353, (b) T. M. Shaikh and S. Arumugam, Eur. J. Org. Chem., 2008, 29, (c) T. H. Nguyen, N. T. T. Chau, A. S. Castanet, K. P. P. Nguyen and J. Mortier, J. Org. Chem., 2007, 72, (d) K. Nemoto, H.Yoshida, N. Egusa, N. Morohashi and T. Hattori, J. Org. Chem., 200, 75, (e) C. M. Yang and Y. T. Chung, Tetrahedron Lett., 204, 55, (f) S. Kumar, S. K. Dixit and S. K. Awasthi, Tetrahedron Lett., 204, 55, (g) C. Boersch, E. Merkul and T. J. J. Müller, Angew. Chem., Int. Ed., 20, 50, (h) B. Pieber, T. Glasnov and C. O. Kappe, RSC Adv., 204, 4, (i) H. -S. Li, G. Liu, J.Org. Chem., 204, 79, (j) Zheng, R.; Zhou, Q.; Gu, H.; Jiang, H.; Wu, J.; Jin, Z.; Han, D.; Dai, G.; Chen, R. Tetrahedron Letters 204, 55, (k) Q. Jiang, A. Zhao, B. Xu, J. Jia, X. Liu, and C. Guo, J. Org. Chem., 204, 79, (l) C. D. Gabbutt, B. M. Heron, A. C. Instone, P. N. Horton, M. B. Hursthouse, Tetrahedron., 2005, 6, (a) Q. Jiang, A. Zhao, B. Xu, J. Jia, X. Liu, and C. Guo, J. Org. Chem., 204, 79, (b) X. -F. Bai, F. Ye, L. -S. Zheng, G. -Q. Lai, C. -G. Xia, L. -W. Xu, Chem. Commun. 202, 48, (c) H. Jia, G. Dai, J. Weng, Z. Zhang, Q. Wang, F. Zhou, L. Jiao, Y. Cui, Y. Ren, S. Fan, J. Zhou, W. Qing, Y. Gu, J. Wang, Y. Sai, W. Su, Journal of Medicinal Chemistry 204, 57, (d) X. Lei, C.-H. Jiang, X. Wen, Q.-L. Xu, H. Sun, RSC Advances 205, 5, (e) R.A.Vishwakarma, S.D. Sawant, P.P. Singh, A.H. Dar, P.R.Sharma, A.K.Saxena, A..Nargotra, K.A. Arvind, M. Ramesh, A.K.Qazi, A. Hussain, C. Nuyan, US A,
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