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133.1, 129.5, 129.3 (×2), 128.8 (×2), 128.2, 123.6, 43.1, 31.9, 29.6 (×4), 29.5, 29.4, 29.3, 28.9, 26.4, 22.6, 14.1. HRMS (EI): C22H34ClN3, calcd 375.2441, found: 375.2446. 5-(4-Chlorophenyl)-1-tetradecyl-1H-imidazol-2-amine (BS-127) H 2N N N C 14H 29 Yield: 51 %. Mp: 82-83 ° C. 1 H NMR (300 MHz, CDCl3): δ = 7.35 (d, J = 8.5 Hz, 2H), 7.23 (d, J = 8.7 Hz, 2H), 6.67 (s, 1H), 4.00 (br, 2H), 3.72 (t, J = 7.3 Hz, 2H), 1.55 (m, 2H), 1.17 (m, 22H), 0.87 (m, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =149.1, 133.1, 129.5, 129.3 (×2), 128.8 (×2), 128.2, 123.6, 43.1, 31.9, 29.6 (×5), 29.5, 29.4 (×2), 29.0, 26.4, 22.7, 14.1. HRMS (EI): C23H36ClN3, calcd 389.2598, found: 389.2602. 5-(4-Chlorophenyl)-1-cyclohexyl-1H-imidazol-2-amine (BS-128) H 2N N N Yield: 37 %. Mp: 179-181 ° C. 1 H NMR (300 MHz, CDCl3): δ = 7.35 (d, J = 8.4 Hz, 2H), 7.18 (d, J = 8.4 Hz, 2H), 6.60 (s, 1H), 4.00 (br, 2H), 3.81 (m, 1H), 1.87 (m, 6H), 1.66 (m, 1H), 1.23 (m, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =148.8, 133.2, 130.2 (×2), 129.8, 128.9, 128.7 (×2), 123.7, 55.2, 31.2(×2), 25.9 (×2), 25.1. HRMS (EI): C15H18ClN3, calcd 275.1189, found: 275.1187. 5-(4-Chlorophenyl)-1-pentyl-1H-imidazol-2-amine (BS-129) H 2N N N C5H11 Yield: 38 %. Mp: 96-98 ° C. 1 H NMR (300 MHz, CDCl3): δ = 7.35 (d, J = 8.4 Hz, 2H), 7.23 (d, J = 8.8 Hz, 2H), 6.67 (s, 1H), 4.08 (br, 2H), 3.73 (t, J = 7.3 Hz, 2H), 1.58 (m, 2H), 1.22 (m, 4H), 0.82 (t, J = 6.6 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =149.3, 133.0, 129.5, 129.3 (×2), 128.8 (×2), 128.2, 123.4, 43.2, 29.3, 28.6, 22.1, 13.8. HRMS (EI): C14H18ClN3, calcd 263.1189, found: 263.1185. Cl Cl Cl
5-(4-Chlorophenyl)-1-cyclobutyl-1H-imidazol-2-amine (BS-130) H 2N N N Yield: 40%. Mp: 156-159 ° C. 1 H NMR (300 MHz, CDCl3): δ = 7.33 (d, J = 8.4 Hz, 2H), 7.19 (d, J = 8.5 Hz, 2H), 6.57 (s, 1H), 4.55 (m, 1H), 4.00 (br, 2H), 2.47 (m, 2H), 2.27 (m, 2H), 1.76 (m, 2H). 13 C NMR (75.5 MHz, CDCl3): δ =149.4, 133.0, 129.8, 129.7 (×2), 128.6 (×2), 128.4, 123.5, 49.2, 29.5 (×2), 15.0. HRMS (EI): C13H14ClN3, calcd 247.0876, found: 247.0874. 5-(4-Methoxyphenyl)-1-octyl-1H-imidazol-2-amine (BS-199) H 2N N N C8H17 Yield: 56 %. 1 H NMR (300 MHz, CDCl3): δ = 7.25 (m, 2H), 6.95 (d, J = 8.7 Hz, 2H), 6.60 (s, 1H), 3.97 (br s, 2H), 3.84 (s, 3H), 3.70 (t, J = 7.8 Hz, 2H), 1.56 (m, 2H), 1.17 (m, 10H), 0.86 (t, J = 7.05 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =149.2, 131.1, 129.5, 129.3 (×2), 128.8 (×2), 128.2, 123.4, 43.1, 31.6, 29.5, 29.0, 28.9, 26.4, 22.2, 14.0. HRMS (EI): C18H27N3O, calcd 301.4265, found: 301.4271. 5-(4-Fluorophenyl)-1-octyl-1H-imidazol-2-amine (BS-200) H 2N N N C8H17 Yield: 71 %. 1 H NMR (300 MHz, CDCl3): δ = 7.27 (m, 2H), 7.09 (m, 2H), 6.63 (s, 1H), 3.96 (br s, 2H), 3.70 (t, J = 6.8 Hz, 2H), 1.56 (m, 2H), 1.17 (m, 10H), 0.86 (t, J = 7.05 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): C17H24FN3, calcd 289.3910, found: 289.3901. 5-(3,4-Dichlorophenyl)-1-octyl-1H-imidazol-2-amine (BS-201) Cl O F
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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
Page 79 and 80: 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: Yield: 50 %. Mp: 76-78 ° C. 1 H NM
Page 133 and 134: Yield: 66%. 1 H NMR (300 MHz, CDCl3
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
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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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