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2.9.2 General Procedure for the Preparation of Salts. To a solution of 2-substituted aminopyrimidine (6 mmol) and α-bromoacetophenone (7.2 mmol, 1.2 equiv) in acetonitrile (12 mL) was added 4-dimethylaminopyridine (6 mg, 0.05 mmol). After being stirred at 85 °C for 5 h, the reaction mixture was diluted with acetone (20 mL) and the precipitate was filtered and washed with acetone (2×20 mL), ether (2×20 mL) and dried over P2O5 to give salt as a white solid. 10 new compounds were synthesized in similar manner. 2.9.3 General Procedure for the Preparation of Salts. (Microwave) In a 50 mL microwave vial were successively dissolved 2-substituted aminopyrimidine (6 mmol) and α-bromoacetophenone (7.2 mmol, 1.2 equiv) in acetonitrile (12 mL) was added 4-dimethylaminopyridine (6 mg, 0.05 mmol). The reaction tube was sealed, and irradiated in the cavity of a Milestone MicroSYNTH microwave reactor at a ceiling temperature of 80 °C at 100 W maximum power for 30 min. After the reaction mixture was cooled with an air flow for 15 min, the reaction mixture was diluted with acetone (20 mL) and the precipitate was filtered and washed with acetone (2×20 mL), ether (2×20 mL) and dried over P2O5 to give salt as a white solid. 34 new compounds were synthesized in similar manner. 2.9.4 General Procedure for the Preparation of 2-Amino-1H-imidazoles. To a suspension of salt (2 mmol) in MeCN (5 mL) hydrazine hydrate (0.7 mL, 14 mmol of a 64% solution, 7 equiv) was added, and the mixture was irradiated in the sealed Milestone MicroSYNTH microwave reactor for 10 min at a ceiling temperature of 100 °C at 150 W maximum power. After cooling down hydrazine hydrate was evaporated with toluene (3×20 mL). The resulting residue was purified by column chromatography (silica gel; MeOH−DCM 1:4 v/v with 5% of 6M NH3 in MeOH) to afford 2-amino-1H-imidazole as an amorphous material. 12 new compounds were synthesized in similar manner. 2.9.5 General procedure for the one-pot two-step microwave-assisted synthesis of 2-amino-1H-imidazoles. In a microwave vial (10 mL) were successively dissolved in dry MeCN (3 mL) the corresponding 2-aminopyrimidine (4 mmol) and α-bromoketone (4.6 mmol). The reaction tube was sealed and irradiated in a microwave reactor at a ceiling
temperature of 80 °C and a maximum power of 50 W for 30 min. After the reaction mixture was cooled with an air flow for 15 min, hydrazine hydrate (0.9 mL, 28 mmol of a 64% solution, 7 equiv) was added, and the mixture was irradiated at a ceiling temperature of 90 °C and a maximum power of 50 W for another 10 min. After the reaction mixture was cooled, hydrazine hydrate was removed by distillation with toluene (3×20 mL). The resulting residue was purified by column chromatography (silica gel; MeOH-DCM 1:9 v/v with 0.5 % of 6N ammonia in MeOH) to afford 2amino-1H-imidazole as amorphous solid. 10 new compounds were synthesized in similar manner. 2.10 Spectral Characterization N-Cyclooctylpyrimidin-2-amine (BS-024) N N N H Yield: 60%. 1 H NMR (300 MHz, CDCl3): δ = 8.25 (d, J = 4.77 Hz, 2H), 6.46 (t, J = 4.8 Hz, 1H), 5.07 (br s, 1H), 4.04 (m, 1H), 1.93 (m, 2H), 1.63 (m, 12H). 13 C NMR (75.5 MHz, CDCl3): δ =161.6, 158.0 (×2), 110.0, 50.6, 31.7 (×2), 27.5 (×2), 25.3, 23.5 (×2). HRMS (EI): C12H19N3, calcd 205.2994, found: 205.2982. N –Cycloheptylpyrimidin-2-amine (BS-025) N N N H Yield: 64%. 1 H NMR (300 MHz, CDCl3): δ = 8.26 (d, J = 4.77 Hz, 2H), 6.47 (t, J = 4.77 Hz, 1H), 5.09 (br s, 1H), 4.01 (m, 1H), 2.02 (m, 2H), 1.55 (m, 10H). 13 C NMR (75.5 MHz, CDCl3): δ =161.6, 158.0 (×2), 110.0, 51.6, 35.0 (×2), 28.2 (×2), 23.9 (×2). HRMS (EI): C11H17N3, calcd 191.2728, found: 191.2742. N –Heptylpyrimidin-2-amine (BS-026) N N N H C 7H 15 Yield: 87%. 1 H NMR (300 MHz, CDCl3): δ = 8.27 (d, J = 4.8 Hz, 2H), 6.50 (t, J = 4.8 Hz, 1H), 5.07 (br s, 1H), 3.40 (m, 2H), 1.61 (m, 2H), 1.31 (m, 8H), 0.85 (m 3H). 13 C
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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
Page 25 and 26: aromatic amines, Lancini’s group
Page 27 and 28: 1.9 2-Aminoimidazole Alkaloids The
Page 29 and 30: Recently group of Erik 83 described
Page 31 and 32: 1.10 Methods for the preparation of
Page 33 and 34: R 1 O X R 2 NH 2 H 2N NAc R 1 HN R
Page 35 and 36: this manifold, was reported in 1925
Page 37 and 38: Another route to 4(5)-acyl-2-amino-
Page 39 and 40: this series of compounds against th
Page 41 and 42: documented. Extra care is needed be
Page 43 and 44: 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: 2.9 Experimental protocol: 2.9.1 Ge
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 125 and 126: Yield: 52 %. 1 H NMR (300 MHz, CDCl
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5-(4-Chlorophenyl)-1-cyclooctyl-1H-
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Yield: 50 %. Mp: 76-78 ° C. 1 H NM
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5-(4-Chlorophenyl)-1-cyclobutyl-1H-
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Yield: 66%. 1 H NMR (300 MHz, CDCl3
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3.10 Representative NMR spectra 3.1
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3.11 References [1] (a) Alvi K. A,
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Copper Catalyzed Microwave Assisted
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4.1 Introduction There are only a f
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(Table-1, No- 6). Next reaction tem
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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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