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1-Hexyl-5-phenyl-1H-imidazol-2-amine (BS-060) H 2N N N C6H13 Yield: 53 %. 1 H NMR (300 MHz, CDCl3): δ = 7.41-7.30 (m, 5H), 6.67 (s, 1H), 3.98 (br, 2H), 3.75(t, J = 7.4 Hz, 2H), 1.59 (m, 2H), 1.18 (m, 6H), 0.82 (t, J = 6.4 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =149.0, 131.0, 129.4, 128.6 (×2), 128.2 (×2), 127.2, 122.8, 43.1, 31.1, 29.5, 26.1, 22.4, 13.8. HRMS (EI): C15H21N3, calcd 243.1735, found: 243.1730. 1-Nonyl-5-phenyl-1H-imidazol-2-amine (BS-063) H 2N N N C9H19 Yield: 58 %. 1 H NMR (300 MHz, CDCl3): δ = 7.31 (m, 5H), 6.67 (s, 1H), 3.95 (br, 2H), 3.75(t, J = 7.5 Hz, 2H), 1.58 (m, 2H), 1.17 (m, 12H), 0.86 (t, J = 6.6 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =152.6, 134.6, 132.9, 132.1 (× 2), 131.7 (× 2), 130.7, 126.4, 46.6, 35.3, 33.0, 32.8, 32.6, 32.5, 30.0, 26.1, 17.6. HRMS (EI): C18H27N3, calcd 285.2205, found: 285.2222. 5-Phenyl-1-undecyl-1H-imidazol-2-amine (BS-066) H 2N N N C 11H 23 Yield: 52 %. 1 H NMR (300 MHz, CDCl3): δ = 7.42-7.31 (m, 5H), 6.67 (s, 1H), 3.99 (br, 2H), 3.75 (t, J = 7.0 Hz, 2H), 1.59 (m, 2H), 1.17 (m, 16H), 0.87 (t, J = 6.4 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =149.1, 131.0, 129.4, 128.6 (×2), 128.2 (×2), 127.1, 122.9, 43.1, 31.8, 29.5 (× 2), 29.4, 29.3, 29.2, 28.9, 26.4, 22.6, 14.1. HRMS (EI): C20H31N3, calcd 313.2518, found: 313.2512. 1-Dodecyl-5-phenyl-1H-imidazol-2-amine (BS-069) H 2N N N C 12H 25
Yield: 52 %. 1 H NMR (300 MHz, CDCl3): δ = 7.39-7.30 (m, 5H), 6.67 (s, 1H), 3.99 (br, 2H), 3.75 (t, J = 7.2 Hz, 2H), 1.58 (m, 2H), 1.17 (m, 18H), 0.88 (t, J = 6.4 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =149.0, 131.1, 129.4, 128.6 (×2), 128.2 (×2), 127.1, 123.0, 43.1, 31.9, 29.5 (× 3), 29.4, 29.3(× 2), 28.9, 26.4, 22.6, 14.1. HRMS (EI): C21H33N3, calcd 327.2674, found: 327.2663. 5-Phenyl-1-tridecyl-1H-imidazol-2-amine (BS-072) H 2N N N C 13H 27 Yield: 58 %. Mp: 44-46 ° C. 1 H NMR (300 MHz, CDCl3): δ = 7.40-7.31 (m, 5H), 6.67 (s, 1H), 3.99 (br, 2H), 3.75 (t, J = 7.3 Hz, 2H), 1.58 (m, 2H), 1.17 (m, 20H), 0.88 (t, J = 6.4 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =148.9, 131.0, 129.4, 128.6 (×2), 128.2 (×2), 127.1, 122.7, 43.1, 31.9, 29.5 (× 7), 28.9, 26.4, 22.6, 14.1. HRMS (EI): C22H35N3, calcd 341.2831, found: 341.2827. 5-Phenyl-1-tetradecyl-1H-imidazol-2-amine (BS-075) H 2N N N C 14H 29 Yield: 64 %. Mp: 44-46 ° C. 1 H NMR (300 MHz, CDCl3): δ = 7.41-7.30 (m, 5H), 6.67 (s, 1H), 4.00 (br, 2H), 3.75 (t, J = 7.4 Hz, 2H), 1.58 (m, 2H), 1.17 (m, 22H), 0.88 (t, J = 6.3 Hz, 3H). 13 C NMR (75.5 MHz, CDCl3): δ =148.8, 131.0, 129.5, 128.6 (×2), 128.3 (×2), 127.2, 122.8, 43.1, 31.9, 29.6 (× 8), 28.9, 26.4, 22.6, 14.1. HRMS (EI): C23H37N3, calcd 355.2987, found: 355.3016. 1-Cyclohexyl-5-phenyl-1H-imidazol-2-amine (BS-078) H 2N N N Yield: 64 %. Mp: 153-155 ° C. 1 H NMR (300 MHz, CDCl3): δ = 7.42-7.28 (m, 5H), 6.60 (s, 1H), 3.89 (m, 3H), 1.88 (m, 6H), 1.64 (m, 1H), 1.18 (m, 3H). 13 C NMR (75.5
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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
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 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: 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 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
Page 147 and 148: 4.4 Possible Mechanism Regarding th
Page 149 and 150: 4.7 Experimental protocols 4.7.1 Ge
Page 151 and 152: Yield: 69 %. 1 H NMR (300 MHz, CDCl
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
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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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