423491
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Image:
furan (image/png)
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-1,4 dicarbonyl, acid - Nitration-sulphuric acid and nitric acid, acetyl nitrate -Bromination-polybromination, Br2+dioxane, Br2+EtOH -Diels Alder reaction |
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Image:
pyrrole (image/png)
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-Paul-Knorr synthesis-1,4 dicarbonyl + carbonylamine -Hantzsch synthesis-haloketene, amine, ketone -Acid sensitive -Electrophilic substitution- 2 and 3 -Tetrabromination -Weak base-alkylated by alkyl halides or Grignard reagent -Diels Alder- EWG on N and v. reative dieneophile |
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Image:
thiophene (image/png)
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-1,4 dicarbonyl and P2S5 -1,3-diyne and metal sulphide -Most aromatic-electrophilic substitution -Not acid sensitive -No Diels Alder -Friedel Crafts- SnCl4 -Monobromination at 2 -Desulfurisation-Raney nickel catalyst |
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imidazole (image/png)
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-halodiesters, carbonyl amine, amine -Highly basic-stabilised symmetrical cation -Acid imidazoles- stab reagent- -ve imidazole and ketone |
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oxazole (image/png)
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-Fischer oxazole synthesis- cyanohydrin and ketone - Diels Alder followed by retro diels alder to give furan |
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Image:
thiazole (image/png)
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-Claissen condensation of ketone, addition of NaNO2, addition of SO2Cl2, addition of aminosulfide -Ketobromide, aminosulfide |
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Image:
pyrazole (image/png)
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-1,2-dicarbonyl, NH2NH2, loss of water 1,3-dipolar cycloaddtion with nitrile imine |
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Image:
isoxazole (image/png)
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1,3 dicarbonyl, hydroxylamine, loss of water 1,3-dipolar cycloaddition with nitrile oxide and alkyne React with cis alkene to make isoxazoline-lose of double bond in structure |
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Image:
isothiazole (image/png)
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From 1,3,4-oxathiazol-2-one-> [R-C=N-S]-> 1,3-dipolar cycloaddition with alkyne |
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Image:
pyridine (image/png)
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Hanzsch synthesis- 2 x 1,4 dicarbonyl, ketone, amine-> amine replaces carbonyl on one then cyclisation-> loss of 2 hydrogens Guareschi synthesis-> need base + heat, 1,4-dicarbonyl, carbonylaminenitrile Alkylation on N by NaOH and alkyl halide Alkylation on 2 position by CH2N2 Reluctant nitration at 3 position Friedel Crafts acylation at N Nucleophilic aromatic substitution: -Chichibabin reaction with NaNHs- NH2 at 2 position - Displacement of halogens Base- reacts to form pyridinium salts Pyridine N oxide formed by reaction with hydrogen peroxide- can then undergo nitration with nitric acid and sulphuric acid at para position |
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Image:
indole (image/png)
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Fischer Indole Synthesis-> benzene ring-NH-NH2 + ketone-> hydrozone -> ring cyclisation Need acid, loss of water and amine Bischler synthesis Benzene amine and ketobromide -> loss of bromine-> addition of POCl3 and loss of water Madelieng synthesis -> Benzene ring with methyl group and NHCOMe group->ring cyclisation with loss of water Electrophilic substitution occurs at 3 position |
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Image:
quinoline (image/png)
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Friedlander synthesis -> benzene with a amine group and a carbonyl group + ketone Electrophilic substitution at top and bottom of benzene ring Reissert reaction -> inserts carbonyl group on N and CN at 2 positon, acid removes CN group |
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Image:
isoquinoline (image/png)
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Bischer-Napieralski synthesis -> Benzene with a CH2CH2NH2 and chloroketone -> ketone attaches to amine -> addition of POCl3-> formation of ring-> oxidation in air Electrophilic substitution at top and bottom of benzene ring Reissert reaction -> inserts carbonyl group on N and CN at 2 positon, acid removes CN group |
| Reissert reaction |
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