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Quinoline N-oxides (1) react with 2-thiobarbituric acid (2) in Ac2O-DMF or in Ac2O alone to afford regioselectively 2-substituted quinolines (3) or quinolinium ylides (4) depending on the nature of 1 and the reaction conditions.The reaction of quinoline, lepidine, 4-chloroquinoline and 4-methoxyquinoline N-oxide with 2 in Ac2O-DMF at room temperature or at 90 deg C gives the corresponding N-ylides (4).The directive influence of the reaction medium becomes reverse when Ac2O is used alone at room temperature or at 90 deg C.While 3-cyanoquinoline N-oxide (1g) gives only 2-substituted quinoline (3g), 4-morpholino- and 3-bromo-quinoline N-oxides (1e,f) afford N-ylides (4e,f) independently of the reaction conditions.Furthermore, isoquinoline 2-oxide (7) readily reacts with 2 under different conditions to give invariably the 1-substituted isoquinoline (8).Pyridine N-oxide gives only 5-dimethylaminomethylene-2-thiobarbituric acid (9) on reaction with 2 in Ac2O-DMF at room temperature.

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Isoquinoline | C9H701N – PubChem

 

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Reduction of N-oxides with baker’s yeast has been examined.In the reduction of acetylpyridine N-oxides, selective reduction takes place to give chiral pyridylethanol N-oxides.

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Isoquinoline – Wikipedia,
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The invention discloses (iso) quinoline and quinoxaline substituted xanthone and quinoxaline nitrogen oxide as the reaction raw material, and the method (has the advantages): reaction is efficient, the condition is mild, operation is simple. raw materials are easy to obtain, without metal participation . and the quinoxaline nitrogen oxide is prepared, by using a one-pot method under an acidic condition with, iso, quinoxaline nitrogen oxide or quinoxaline nitrogen oxide as a raw material in an acidic condition. (by machine translation)

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A general and facile one-pot procedure for the synthesis of 2-substituted pyridines from the corresponding pyridine-N-oxides and nucleophiles is presented as a mild alternative to SNAr chemistry. A variety of nucleophiles and heterocyclic-N-oxides participate effectively in this transformation, which uses the phosphonium salt, PyBroP, as a means of substrate activation.

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An efficient and convenient procedure for the conversion of pyridine N-oxides to tetrazolopyridines by treatment with 4-toluene sulfonyl chloride and sodium azide in toluene at elevated temperature is described.

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Reduction of N-oxides with baker’s yeast has been examined.In the reduction of acetylpyridine N-oxides, selective reduction takes place to give chiral pyridylethanol N-oxides.

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Isoquinoline – Wikipedia,
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Heteroaryl substituted oxazolinylidene derivatives (3) and (4) were converted by opening of the oxazolinone ring under hydrolytic conditions, followed by decarboxylation into acylaminomethyl derivatives (5) and (6), with hydrazine hydrate into the corresponding hydrazides (7), with liquid ammonia under pressure into amides (8), and with amino acids into dipeptides (9-11).

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The invention discloses a 2, 3 – disubstituted benzo – gamma – pyrone derivatives of the preparation method, the present invention through the substituted acetylenic ketone and quinoline nitrogen oxide by one-step reaction of 2, 3 – disubstituted benzo – gamma – pyrone derivatives, its reaction process through the area between the molecules selective 1, 3 – dipole ring addition, N – O bond breaking reaction, and then molecular […], “one-pot” obtain 2, 3 – disubstituted benzo – gamma – pyrone derivatives. The method of the invention the resulting raw materials are easy, high yield, mild reaction conditions, the reaction time is moderate, wide substrate range, reaction specificity is strong, easy post treatment and green environmental protection. (by machine translation)

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Phthalide-3-carboxylic acid has been decarboxylated in the presence of isoquinoline, 1-chloroisoqinoline and isoquinoline N-oxides to give low yields of compounds resulting from alkylation of the isoquinoline heterocycle at C1 with a phthalidyl group.Attempted Barton decarboxylation-alkylation in the presence of isoquinolinium salts was unsuccessful.

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Reference:
Isoquinoline – Wikipedia,
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