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H 2N N N C8H17 Yield: 64 %. 1 H NMR (300 MHz, CDCl3): δ = 7.47 (d, J = 8.3 Hz, 1H), 7.40 (d, J = 7.98 Hz, 1H), 7.16 (d of d, J = 2.0, 6.2 Hz, 1H), 6.71 (s, 1H), 4.05 (br s, 2H), 3.73 (t, J = 7.68 Hz, 2H), 1.59 (m, 2H), 1.19 (m, 10H), 0.86 (t, J = 7.05 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =149.6, 132.8, 131.1, 131.0, 130.6, 129.5, 127.1, 127.0, 124.2, 43.3, 31.6, 29.5, 29.0, 28.9, 26.4, 22.5, 14.0. HRMS (EI): C17H23Cl2N3, calcd 340.2906, found: 240.2918. 5-(3-Bromophenyl)-1-octyl-1H-imidazol-2-amine (BS-202) H 2N N N C8H17 Yield: 68 %. 1 H NMR (300 MHz, CDCl3): δ = 7.45 (m, 2H), 7.25 (m, 2H), 6.70 (s, 1H), 4.02 (br s, 2H), 3.74 (t, J = 7.71 Hz, 2H), 1.59 (m, 2H), 1.19 (m, 10H), 0.86 (t, J = 6.08 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =149.2, 133.0, 130.8, 130.1 (×2), 128.0, 126.5, 123.8, 122.6, 43.2, 31.6, 29.5, 29.0, 28.9, 26.4, 22.5, 14.0. HRMS (EI): C17H24BrN3, calcd 350.2966, found:250.2978. 5-(Naphthalen-1-yl)-1-octyl-1H-imidazol-2-amine (BS-202) H 2N N N C8H17 Yield: 68 %. 1 H NMR (300 MHz, CDCl3): δ = 7.85 (m, 4H), 7.46 (m, 3H), 6.78 (s, 1H), 4.04 (br s, 2H), 3.83 (t, J = 7.62 Hz, 2H), 1.62 (m, 2H), 1.15 (m, 10H), 0.82 (t, J = 6.99 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =149.1, 133.4, 132.4, 129.5, 128.3, 128.2, 127.9, 127.7, 126.6, 126.4 (×2), 126.0, 123.0, 43.3, 31.6, 29.5, 29.0, 28.9, 26.4, 22.5, 14.0. HRMS (EI): C21H27N3, calcd 321.4592, found: 321.4576. 5-(4-Nitrophenyl)-1-octyl-1H-imidazol-2-amine (BS-204) H 2N N N C8H17 Cl Cl Br NO 2
Yield: 66%. 1 H NMR (300 MHz, CDCl3): δ = 8.27 (d, J = 8.7 Hz, 2H), 7.47 (t, J = 8.7 Hz, 2H), 6.89 (s, 1H), 4.13 (br s, 2H), 3.82 (t, J = 7.8 Hz, 2H), 1.63 (m, 2H), 1.21 (m, 10H), 0.85 (t, J = 6.96 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =163.8, 160.5, 148.7, 130.2, 128.4, 127.0, 122.9, 115.5, 104.7, 43.0, 31.6, 29.5, 29.0, 28.9, 26.4, 22.5, 14.0. HRMS (EI): C17H24N4O2, calcd 316.3981, found: 316.3993. 5-(4'-Nitrobiphenyl-4-yl)-1-octyl-1H-imidazol-2-amine (BS-205) H 2N N N C8H17 Yield: 52 %. 1 H NMR (300 MHz, CDCl3): δ = 8.33 (m, 1H), 7.78-7.35 (m, 6H), 7.13 (m 1H), 6.77 (s, 1H), 4.07 (br s, 2H), 3.79 (m, 2H), 1.63 (m, 2H), 1.19 (m, 10H), 0.84 (m, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =163.8, 160.5, 148.7, 130.2, 128.4, 127.0, 122.9, 115.5, 104.7, 43.0, 31.6, 29.5, 29.0, 28.9, 26.4, 22.5, 14.0. HRMS (EI): C23H28N4O2, calcd 392.4940, found:392.4928. NO 2 5-(4-(Methylsulfonyl)phenyl)-1-octyl-1H-imidazol-2-amine (BS-206) H 2N N N C8H17 SO 2Me Yield: 61 %. 1 H NMR (300 MHz, CDCl3): δ = 7.97 (d, J = 8.1 Hz, 2H), 7.51 (d, J = 7.98 Hz, 2H), 6.83 (s, 1H), 4.09 (br s, 2H), 3.82 (t, J = 7.68 Hz, 2H), 3.09 (s 3H), 1.62 (m, 2H), 1.21 (m, 10H), 0.86 (t, J = 7.05 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =150.7, 138.1, 136.6, 127.9 (×2), 127.6, 127.4 (×2), 126.0, 44.5, 43.6, 31.6, 29.6, 29.0, 28.9, 26.5, 22.5, 14.0. HRMS (EI): C18H27N3O2S, calcd 349.4909, found: 349.4920. 5-(4-(Methylthio)phenyl)-1-octyl-1H-imidazol-2-amine (BS-207) H 2N N N C8H17 Yield: 40 %. 1 H NMR (300 MHz, CDCl3): δ = 7.33-7.22 (m, 4H), 6.65 (s, 1H), 4.00 (br s, 2H), 3.73 (t, J = 7.98 Hz, 2H), 2.51 (s, 3H), 1.58 (m, 2H), 1.18 (m, 10H), 0.86 (t, J = 6.99 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =163.8, 160.5, 148.7, 130.2, SMe
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Saurashtra University Re - Accredit
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JANUARY-2011 Statement under O. Ph.
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Acknowledgment This thesis arose in
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since I was a child. My Mother Hans
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CHAPTER - 2 Microwave Assisted Synt
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5.5 Results and discussion 156 5.6
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Ms Mesyl MW Microwave NBS N-bromosu
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1. Microwave Assisted Organic Synth
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1.4 Heating Mechanism In microwave
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1.5. Effects of solvents Every solv
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1.7 Application of microwave in org
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aromatic amines, Lancini’s group
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1.9 2-Aminoimidazole Alkaloids The
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Recently group of Erik 83 described
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1.10 Methods for the preparation of
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R 1 O X R 2 NH 2 H 2N NAc R 1 HN R
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this manifold, was reported in 1925
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Another route to 4(5)-acyl-2-amino-
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this series of compounds against th
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documented. Extra care is needed be
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Very recently the research group of
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OH a,b O N H2N N Boc N 3 H N R N N
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1.12.2 Biofilm Growth Cycle 1) Plan
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can survive both the onslaught of a
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[26] Leadbeater, N. E. (2004) Chemi
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[86] Kreutzberger, A. (1962) J. Org
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Microwave Assisted Synthesis & Stru
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2.1 Introduction As described in ch
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2.3 Proposed Mechanism: Regarding t
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No. 12 60 120 traces 84 a All react
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the development of biofilm related
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In first instance, a series of 2-hy
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Br N N N R 1 OH Br N N N R 1 OH Fig
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do have a very strong effect agains
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2.6 Conclusion In the present study
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2.8 Biological assays 2.8.1 Static
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2.9 Experimental protocol: 2.9.1 Ge
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temperature of 80 °C and a maximum
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29.5,29.4, 29.2, 27.0, 22.6, 14.1.
Page 81 and 82: Yield: 78 %. 1 H NMR (300 MHz, CDCl
Page 83 and 84: N Br N N C 14H 29 OH Yield: 72 %. 1
Page 85 and 86: (75.5 MHz, CDCl3): δ = 167.7, 154.
Page 87 and 88: N Br N N C 14H 29 OH Cl Yield: 90 %
Page 89 and 90: 2-(3,4-Dichlorophenyl)-2-hydroxy-1-
Page 91 and 92: N Br N N C 8H 17 OH NO 2 Yield: 49
Page 93 and 94: C3H7 HN N N H Cl Cl Yield : 70 %. 1
Page 95 and 96: (s, 1H), 3.16 (s, 3H), 1.80 (m, 2H)
Page 97 and 98: 5-(4’-Nitrobiphenyl-4-yl)-N-octyl
Page 99 and 100: 2.11 Representative NMR spectra 2.1
Page 101 and 102: 2.11.3 10.4329 0.7429 151.5720 10.0
Page 103 and 104: [21] Matz C, McDougald D, Moreno A.
Page 105 and 106: Chapter-3 Structure Activity Relati
Page 107 and 108: imidazoles, where the addition of a
Page 109 and 110: 3.4 Result and Discussion It was fo
Page 111 and 112: No. H 2N Compound Code N N C8H17 R1
Page 113 and 114: medium used in the set-up to monito
Page 115 and 116: H 2N N N N H2N N R R Figure-1 Effec
Page 117 and 118: 3.5.3 Cyclo-alkyl 2-aminoimidazoles
Page 119 and 120: 3.6. Conclusion In the present stud
Page 121 and 122: 3.8. Experimental protocols 3.8.1 G
Page 123 and 124: 122.6, 54.6, 33.3(×2), 27.3 (×2),
Page 127 and 128: 5-(4-Chlorophenyl)-1-cyclooctyl-1H-
Page 129 and 130: Yield: 50 %. Mp: 76-78 ° C. 1 H NM
Page 131: 5-(4-Chlorophenyl)-1-cyclobutyl-1H-
Page 135 and 136: 3.10 Representative NMR spectra 3.1
Page 137 and 138: 3.11 References [1] (a) Alvi K. A,
Page 139 and 140: Copper Catalyzed Microwave Assisted
Page 141 and 142: 4.1 Introduction There are only a f
Page 143 and 144: (Table-1, No- 6). Next reaction tem
Page 145 and 146: No. Product, Yield b (%) No. Produc
Page 147 and 148: 4.4 Possible Mechanism Regarding th
Page 149 and 150: 4.7 Experimental protocols 4.7.1 Ge
Page 153 and 154: 1-(3-Azidopropyl)-2-(3,4-dichloroph
Page 155 and 156: Yield: 84 %. 1 H NMR (300 MHz, DMSO
Page 161 and 162: 1H), 1.66 (m, 6H), 1.70 (m, 2H). 13
Page 163 and 164: 5.48 Hz, 2H), 3.59 (m, 2H), 3.16 (d
Page 165 and 166: 4.10 References [1] For a general r
Page 167 and 168: Crystal and Molecular Structure Ana
Page 169 and 170: 5.1 Introduction The membrane efflu
Page 171 and 172: oscillation range of 5˚ and proces
Page 173 and 174: C12-C13 1.372(4) C32-C37 1.390(3) C
Page 175 and 176: Fig.-3: Packing of the molecules wh
Page 177 and 178: 1 H NMR (400 MHz CDCl3): δ = 7.57-
Page 179 and 180: 5.9.2 13 C spectra of bs-DP-7
Page 181 and 182: SUMMARY The work represented in the
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CONFERENCES/SEMINARS/WORKSHOPS ATTE
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PUBLICATIONS [1] One-Pot Microwave-
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Scheme 2 Competitive formation of 1
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Table 2 continued 9 10 11 12 N hydr
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8. Colson G, Raboult L, Lavelle F,
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