Download (8Mb) - Etheses - Saurashtra University

More documents

Recommendations

Info

2.2 Reaction scheme: 2.2.1 2-amino pyramidine: (Scheme-1) N TEA, EtOH N R NH2 R N Cl MW N N 120 H o + C, 25 min 2.2.2 Synthesis of substituted 2-amino 1 H-imidazole. (Scheme-2) N N N 64% N2H4 100 °C, 10 min R N N + Br H R1 N MeCN H MW O 80 °C, 30 min Br 1 OH R2 MeCN MW R 2 2.2.3 One-Pot approach: (Scheme-3) N R1 N N H + Br O H R 2 1.MW, 80 °C MeCN, 30 min 2. N2H4, MW 90 °C MeCN, 10 min R 1 HN N N H R 2 R 1 HN N N H R 2
2.3 Proposed Mechanism: Regarding the mechanism of the transformation of 2-hydroxy-2,3-dihydro-1Himidazo[1,2-a]pyrimidinium salts into 2-amino-1H-imidazoles, we presume that the reaction proceeds via an unusual Dimroth-type rearrangement 14-16 (Scheme-4). Scheme-4: Proposed Mechanism for the Dimroth-type Rearrangement of 2- Hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidinium Salts III-12 N N N R1 Br OH R 2 R3 N N R 2 NH 2 R1 OH R 3 N2H4 fast HN NH R 1 HN R 2 H 2NHN O R 3 N N N R1 OH R 2 R3 R 1HN N N H H 2NHN R 2 OH R 3 N N N R1 OH R 2 R3 1 A B - H 2O slow R 1HN C D E 2 In the first step, the 2-hydroxy-2,3-dihydroimidazo[1,2-a]pyrimidinium salt (1) undergoes cleavage of the pyrimidine ring, resulting in the generation of pyrazole and 2-amino-5-hydroxyimidazolidine (C), which is in equilibrium with the open form (D). This can cyclize again leading to the isomeric 2-amino-5(4)-hydroxyimidazolidines (E). Both isomers (C) and (E) were detected by mass-spectrometry. Final dehydratation upon microwave irradiation, results in the rearranged 2-amino-1Himidazoles 2. This dehydratation step, as judged by mass-spectrometry, was found to be the slowest step of the transformation. While some 2-amino-5(4)hydroxyimidazolidines (E) lost water spontaneously at room temperature, other required higher temperature upon microwave irradiation. Therefore all reactions were run at 100 °C, preventing the sequence from stopping after the first step. - N H N N H N R 2 R 3
Page 1 and 2:
Saurashtra University Re - Accredit
Page 3:
JANUARY-2011 Statement under O. Ph.
Page 7 and 8: Acknowledgment This thesis arose in
Page 9 and 10: since I was a child. My Mother Hans
Page 11 and 12: CHAPTER - 2 Microwave Assisted Synt
Page 13 and 14: 5.5 Results and discussion 156 5.6
Page 15 and 16: Ms Mesyl MW Microwave NBS N-bromosu
Page 17 and 18: 1. Microwave Assisted Organic Synth
Page 19 and 20: 1.4 Heating Mechanism In microwave
Page 21 and 22: 1.5. Effects of solvents Every solv
Page 23 and 24: 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: 2.1 Introduction As described in ch
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 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
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 157 and 158:
Page 159 and 160:
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
Page 183 and 184:
CONFERENCES/SEMINARS/WORKSHOPS ATTE
Page 185:
PUBLICATIONS [1] One-Pot Microwave-
Page 200 and 201:
Scheme 2 Competitive formation of 1
Page 202 and 203:
Table 2 continued 9 10 11 12 N hydr
Page 204:
8. Colson G, Raboult L, Lavelle F,
show all

Download (8Mb) - Etheses - Saurashtra University

Create successful ePaper yourself

Delete template?

Save as template?