- Synthesis and characterization of substituted 4-methoxy-1H-quinolin-2- thiones
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The synthesis of various substituted 4-methoxy-1H-quinolin-2-thiones from various substituted aniline with malonic acid, phosphorousoxychloride, sodium methoxide glacial acetic acid and thiourea under different conditions is described. All these substituted 4-methoxy-1H-quinolin-2-thiones were synthesized from four steps; the first step involved the synthesis of substituted 2,4-dichloro quinoline from aniline (substituted), with malonic acid and phosphorous-oxychloride. In the second step, the substituted 2,4-dichloro compound was heated with freshly prepared methanolic sodium methoxide solution to give 2,4-dimethoxy quinoline compounds, it was then refluxed with glacial acetic acid and hydrochloric acid to get the substituted 4-methoxy-1H-quinolin- 2-one. The final steps involves with an objective of introducing a chloro in the position 2 of the quinolone system, the substituted 4-methoxy-1H-quinolin-2-one was refluxed with distilled PoCl3 chloroform. The substituted 2-chloro-4-methoxy quinoline was then refluxed with thiourea and alcohol to get substituted 4-methoxy-1H-quinolin-2-thiones. The purity of the synthesized compound was judged by their C, H and N analysis and the structure was analyzed on the basics of mass, FT-IR and 1H NMR.
- Ramasamy,Balasubramaniam,Mohan
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p. 4726 - 4728
(2012/09/07)
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- Synthesis and characterization of substituted 4-methoxy-1H-quinolin-2-ones
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An efficient method for the synthesis of various substituted 4- methoxy-1H-quinolin-2-ones from various substituted aniline with malonic acid, phosphorous oxychloride, sodium methoxide and glacial acetic acid under different conditions is described. The title compounds were synthesized from three steps; the first step involved the synthesis of substituted 2, 4-dichloro quinoline from aniline (substituted), with malonic acid and phosphorousoxychloride. In the second step, the substituted 2, 4 dichloro compounds was heated with freshly prepared methanolic sodium methoxide solution to give 2, 4-dimethoxy quinoline compounds, it was then refluxed with glacial acetic acid and hydrochloric acid to give the titled compounds in the final step. The purity of the synthesized compounds was confirmed by their C, H and N analysis and the structure was analyzed on the basics of Mass, FT-IR and 1H NMR.
- Ramasamy,Balasubramaniam,Mohan
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p. 1066 - 1070
(2011/11/29)
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- Synthesis of (+)-myrtopsine, (+)-7,8-dimethoxymyrtopsine, and related 2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methyl-ethyl)benzofuran natural products
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The first syntheses of myrtopsine (8t) and 7,8-dimethoxymyrtopsine (9t) have been carried out by halogen-metal exchange of 3-iodo-4-methoxy-quinolin-2(1H)-ones (15) and (21) with i-PrMgCl followed by addition of 3,3-dimethyloxirane-2-carboxaldehyde (1). A two-step sequence leads selectively to trans-2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methylethyl)benzofurans (7t), (8t), (9t), (28), and (32) by conversion of a 2-iodophenol or a 3-iodo-4-methoxyquinolin-2(1H)-one to an aryl Grignard reagent and addition of 3-methyl-2-butenal, followed by threo selective epoxidation of the resulting allylic alcohol and cyclization with inversion.
- Snider, Barry B.,Wu, Xiaoxing
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p. 279 - 294
(2008/04/18)
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- Demethylation of 2,4-dimethoxyquinolines: the synthesis of atanine.
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The synthesis of the quinoline alkaloid atanine 6, by selective demethylation of the 2,4-dimethoxyquinoline 11 is presented. An alternative demethylation utilising a thiolate anion leads to the regioisomeric 4-hydroxyquinoline 13.
- Jones, Keith,Roset, Xavier,Rossiter, Sharon,Whitfield, Philip
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p. 4380 - 4383
(2007/10/03)
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