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Yield : 72 %. 1 H NMR (300 MHz, DMSO-d6): δ = 10.52 (br s, 1H), 7.82 (s, 1H), 7.58 (m, 1H), 7.50 (d, J = 8.13 Hz, 1H), 7.22 (s, 1H), 5.78 (m, 1H), 3.11 (m, 2H), 1.51 (m, 2H), 1.28 (m, 10H), 0.85 (t, J = 6.94 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 339.1269, found:. 339.1279. 5-(3-Bromophenyl)-N-octyl-1H-imidazol-2-amine (BS-261) C 8H 17 N H N N H Br Yield : 79 %. 1 H NMR (300 MHz, DMSO-d6): δ = 10.49 (br s, 1H), 7.79 (s, 1H), 7.59 (s, 1H), 7.22 (m, 1H), 7.14 (s, 1H), 5.73 (t, J = 5.66 Hz, 1H), 3.11 (m, 2H), 1.51 (m, 2H), 1.25 (m, 10H), 0.84 (t, J = 6.69 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 349.1154, found:. 249.1138. 5-(Naphthalen-1-yl)-N-octyl-1H-imidazol-2-amine (BS-262) C 8H 17 N H N N H Yield : 68 %. 1 H NMR (300 MHz, DMSO-d6): δ = 10.53 (br s, 1H), 8.05 (s, 1H), 7.80 (m, 3H), 7.39 (m, 3H), 7.17 (s, 1H), 5.73 (m, 1H), 3.16 (m, 2H), 1.54 (m, 2H), 1.26 (m, 10H), 0.83 (t, J = 6.86 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:. 321.4578. 5-(4-Nitrophenyl)-N-octyl-1H-imidazol-2-amine (BS-263) C 8H 17 N H N N H NO 2 Yield : 66 %. 1 H NMR (300 MHz, DMSO-d6): δ = 10.74 (br s, 1H), 8.12 (d, J = 8.92 Hz, 2H), 7.84 (d, J = 8.92 Hz, 2H), 7.43 (s.1H), 5.91 (t, J = 5.54 Hz, 1H), 3.16 (m, 2H), 1.52 (m, 2H), 1.25 (m, 10H), 0.85 (t, J = 6.75 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 316.1899, found:.316.1909.
5-(4’-Nitrobiphenyl-4-yl)-N-octyl-1H-imidazol-2-amine (BS-264) C 8H 17 N H N N H NO 2 Yield : 75 %. 1 H NMR (300 MHz, DMSO-d6): δ = 10.53 (br s, 1H), 8.27 (d, J = 8.71 Hz, 2H), 7.96 (d, J = 8.71 Hz, 2H), 7.75 (s.4H), 7.18 (s. 1H), 5.76 (t, J = 5.88 Hz, 1H), 3.16 (m, 2H), 1.53 (m, 2H), 1.26 (m, 10H), 0.86 (t, J = 6.75 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): C23H28N4O2, calcd 392.2212, found:.392.2201. 5-(4-(Methylsulfonyl)phenyl)-N-octyl-1H-imidazol-2-amine (BS-265) C 8H 17 N H N N H O S O Yield : 54 %. 1 H NMR (300 MHz, DMSO-d6): δ = 10.62 (br s, 1H), 7.84 (d, J = 8.55 Hz, 2H), 7.76 (d, J = 8.35 Hz, 2H), 7.32 (s.1H), 5.83 (t, J = 5.97 Hz, 1H), 3.16 (m, 5H), 1.52 (m, 2H), 1.25 (m, 10H), 0.85 (t, J = 6. 56 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:.249.4918. N-Isobutyl-5-(4-nitrophenyl)-1H-imidazol-2-amine (BS-292) N H N N H NO 2 Yield : 70 %. 1 H NMR (300 MHz, DMSO-d6): δ = 10.69 (br s, 1H), 8.12 (d, J = 9.02 Hz, 2H), 7.84 (d, J = 8.50 Hz, 2H), 7.42 (s, 1H), 5.99 (t, J = 5.93 Hz, 1H), 2.99 (t, J = 6.44 Hz, 2H), 1.83 (m, 1H), 0.89 (d, J = 6.70 Hz, 6H). 13 C NMR (75.5 MHz, DMSOd6): δ =152.2 (×2), 143.8, 141.6, 123.9 (×2), 123.3, 104.1 (×2), 50.4, 27.9, 20.1 (×2). HRMS (EI): C13H16N4O2, calcd 260.1273, found: 260.1287 N-Isobutyl-5-phenyl-1H-imidazol-2-amine (BS-293) N H N N H
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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
Page 45 and 46: OH a,b O N H2N N Boc N 3 H N R N N
Page 47 and 48: 1.12.2 Biofilm Growth Cycle 1) Plan
Page 49 and 50: can survive both the onslaught of a
Page 51 and 52: [26] Leadbeater, N. E. (2004) Chemi
Page 53 and 54: [86] Kreutzberger, A. (1962) J. Org
Page 55 and 56: Microwave Assisted Synthesis & Stru
Page 57 and 58: 2.1 Introduction As described in ch
Page 59 and 60: 2.3 Proposed Mechanism: Regarding t
Page 61 and 62: No. 12 60 120 traces 84 a All react
Page 63 and 64: the development of biofilm related
Page 65 and 66: In first instance, a series of 2-hy
Page 67 and 68: Br N N N R 1 OH Br N N N R 1 OH Fig
Page 69 and 70: do have a very strong effect agains
Page 71 and 72: 2.6 Conclusion In the present study
Page 73 and 74: 2.8 Biological assays 2.8.1 Static
Page 75 and 76: 2.9 Experimental protocol: 2.9.1 Ge
Page 77 and 78: 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: (s, 1H), 3.16 (s, 3H), 1.80 (m, 2H)
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 125 and 126: Yield: 52 %. 1 H NMR (300 MHz, CDCl
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 and 132: 5-(4-Chlorophenyl)-1-cyclobutyl-1H-
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
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4.4 Possible Mechanism Regarding th
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4.7 Experimental protocols 4.7.1 Ge
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Yield: 69 %. 1 H NMR (300 MHz, CDCl
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1-(3-Azidopropyl)-2-(3,4-dichloroph
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Yield: 84 %. 1 H NMR (300 MHz, DMSO
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1H), 1.66 (m, 6H), 1.70 (m, 2H). 13
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5.48 Hz, 2H), 3.59 (m, 2H), 3.16 (d
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4.10 References [1] For a general r
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Crystal and Molecular Structure Ana
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5.1 Introduction The membrane efflu
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oscillation range of 5˚ and proces
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C12-C13 1.372(4) C32-C37 1.390(3) C
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Fig.-3: Packing of the molecules wh
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1 H NMR (400 MHz CDCl3): δ = 7.57-
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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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