- Synthesis of 5-ethyl-8-oxo-5.8-dihydro-1,3-dioxolo [4,5-g] quinolines and related compounds
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Condensation of N-ethyl-3,4-methylenedioxyaniline 1 with diethyl ethoxymethylenemalonate 2 gave the unsaturated ester 3 which on thermal cyclization in refluxing diphenyl oxide gave ester 4. The ester on basic hydrolysis formed free acid 5 which upon treatment with thionyl chloride gave the acid chloride 6. Treatment of 6 with o-phenylenediamine, hydrazine hydrate, ammonia, urea and thiourea gave the amides (7-11). CS2 treatment in presence of KOH on 8 gave 12. 7-12 were prepared by conventional as well as under microwave irradiation. These compounds have been characterized on the basis of elemental analysis, IR, NMR and MS data.
- Pednekar, Suhas,Pandey, Anil Kumar
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p. 357 - 360
(2011/12/16)
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- Microwave-assisted synthesis of quinolone derivatives and related compounds
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(Chemical Equation Presented) The Gould-Jacob type of reaction for the synthesis of ethyl 5-ethyl-8-oxo-5,8-dihydro-[1,3]-dioxolo[ 4,5-g]quinoline-7- carboxylate 4 has been carried out conventionally by the condensation between N-ethyl-3,4-methylenedioxyaniline 1 and diethyl ethoxymethylenemalonate 2 gave the unsaturated ester 3 and thermal cyclization in refluxing diphenyl oxide gave quinolone ethyl ester 4 and the results obtained were compared with single step microwave irradiation under solvent free conditions for the synthesis of 4. The esters on basic hydrolysis formed free acid 5, which, upon treatment with thionyl chloride gave the acid chloride 6. Treatment of acid chloride with o-phenylenediamine, hydrazine hydrate, ammonia, urea, and thiourea gave the amides (7-11). CS2 treatment in presence of KOH on 8 gave 12. We prepared 7-12 derivatives by conventional as well as microwave irradiation. These compounds have been characterized on the basis of IR, 1H NMR, MS, and elemental analysis. All the compounds prepared herein were screened for their antibacterial activity. Compounds 4, 5 possess promising antibacterial activity and compound 8 showed significant antibacterial activity.
- Pednekar, Suhas,Pandey, Anil Kumar
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experimental part
p. 1104 - 1108
(2010/11/03)
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- Preparation of 1-(lower alkyl)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acids
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A process for producing a compound of the formula: SPC1 Wherein Z is CH or N; R is a lower alkyl group, a lower alkenyl group, a cycloalkyl group or a hydroxyalkyl group; R1 is a hydrogen atom or lower alkyl group; when Z is N, R2, R3 and R4 are a hydrogen atom, a halogen atom a lower alkyl group, a lower alkoxyl group, a lower hydroxyalkyl group, a lower acyloxyalkyl group, trihalogenoalkyl group, a carboxyl group, a cyano group, or an aralkyl group; when Z is CH, R2, R3 and R4 are a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group, a trihalogenoalkyl group, a cyano group, a nitro group, an alkylmercapto group, a lower alkylenedioxy group, or a lower alkylene bridge attached to the quinoline nucleus, which comprises heating a compound of the formula SPC2 Wherein R, R1, R2, R3, R4 and Z are as defined above, followed, if desired, by hydrolyzing the product obtained, is disclosed. The product is useful as an antibacterial agent. An intermediate having the formula: SPC3 Wherein A is OR or a halogen atom, and R, R1, R2, R3, R4 and Z are as defined above, and a process for its preparation are also disclosed.
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