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Synthesis, Reactions, and Medicinal Uses of Acridine

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  Synthesis, Reactions, and Medicinal Uses of Acridine   Acridine is a three-membered fused heterocyclic system containing Nitrogen as a heteroatom at the 10th position. Two benzene rings are fused to the "b" and "e" sides of pyridine. Other names for acridine are 2,3-Benzoquinoline and Dibenzo[b,e]pyridine. Physical properties: Colour: white State: powder(solid) Melting point: 106 - 110  o C Boiling point: 344.86  o C Solubility: Slightly soluble in hot water and soluble in organic solvents. Structure and Aromaticity: Acridine is a planar molecule, all atoms are  sp 2  hybridised. Unhybridised p-orbitals sidewise overlap to form pi bonds. Acridine contains seven double bonds and 14 delocalised pi electrons, following the huckles rule(4n+2)pi electrons (where n=3). Hence acridine is aromatic. Synthesis of Acridine: 1. Ulmann synthesis:  2-chlorobenzoic acid reacts with aniline in the presence of sodium hydroxide give diphenylamino-2-carboxylic acid(DPCA).  (i) DPCA
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Synthesis, Reactions, and Medicinal Uses of Isoquinoline

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  Synthesis, Reactions, and Medicinal Uses of Isoquinoline  Isoquinoline is a bicyclic hetero-aromatic compound having nitrogen at the second position as heteroatom. It is also called benzo[c]pyridine, the benzene is fused with the "c" side of pyridine. another name for isoquinoline is 2-azanaphthalene. Physical properties: Colour: colourless State: liquid Melting point: 26 - 28  o C Boiling point: 242  o C Solubility: Slightly soluble in water and soluble in organic liquids and dilute acids. Structure and Aromaticity: All atoms in Isoquinoline are  sp 2  hybridised and have a planar structure. Unhybridised p-orbitals sidewise overlap to form five pi bonds. Isoquinoline contains a total of ten delocalised pi electrons, following the huckles rule hence quinoline is an Aromatic. Resonance structures: Synthesis of Isoquinoline: 1. Bischler-Napieralski synthesis:  2-aryl ethanamines react with acyl chloride to give an amide, which upon treated with phosphorus pentoxide or phospho
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Synthesis, Reactions and Medicinal Uses of Quinoline

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  Synthesis, Reactions, and Medicinal Uses of Quinoline          Quinoline is a bicyclic hetero-aromatic compound having nitrogen at the first position as heteroatom. Physical properties: Colour: colourless State: liquid Melting point: -15  o C Boiling point: 237  o C Solubility: Slightly soluble in water and soluble in organic liquids. Structure and Aromaticity: Quinoline is a fused ring system of pyridine and benzene. All atoms in quinoline are  sp 2  hybridised and have a planar structure. Unhybridised p-orbitals sidewise overlap to form five pi bonds. Quinoline contains a total of ten delocalised pi electrons, follows the huckles rule hence quinoline is an Aromatic. Resonance structures: Synthesis of Quinoline: 1. Friedlander Synthesis: O-amino benzaldehyde reacts with carbonyl compound with active methylene compound in presence of alcoholic NaOH give Quinoline. 2. Knorr quinoline Synthesis:  Condensation of aniline with ketoester gives anilide intermediate, which further cyclizati
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