Direct introduction of acetylene moieties into azines by SNH methodology

Tetrahedron Letters

Volumn 50, Issue 13, 2009, Pages 1444-1446

  Prokhorov, Anton M ^a   Makosza, Mieczysław ^b   Chupakhin, Oleg N ^a,c  

^a URAL FEDERAL UNIVERSITY   (Russian Federation)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^c INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZINE 4 OXIDE; 1,2,4 TRIAZINE DERIVATIVE; ACETYLENE DERIVATIVE; ANION; BENZENE DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROGEN; LITHIUM; OXIDE; PHENYLETHYNYLAZINE; POTASSIUM; PYRIDINE 1 OXIDE; QUINOLINE; QUINOXALINE; UNCLASSIFIED DRUG;

ACYLATION; AROMATIZATION; ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; METHODOLOGY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 59649115624     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.070     Document Type: Article

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21. Procedure A for the synthesis of the ethynyl azines 2a-g: A solution of lithium phenylacetylide in THF, prepared by addition of butyllithium (1.05 mmol) to a solution of phenylacetylene (1 mmol) in 10 ml of THF, was added with stirring to a solution of N-oxide 1 (1 mmol) in 10 ml of THF at -50 °C under an argon atmosphere. After 10 min, acetyl chloride (1.05 mmol) was added to the reaction mixture at the same temperature. The solvent was removed, the residue was dissolved in chloroform, and the corresponding ethynylazine was isolated by column chromatography. Procedure B. A solution of N-oxide 1 (1 mmol) in 10 ml of dry DMF was added with stirring to a suspension of potassium phenylacetylide at -20 °C under an argon atmosphere, which was prepared by addition of phenylacetylene (1 mmol) to a suspension of potassium tert-butoxide (2 mmol) in 10 ml of dry DMF. After 30 min, acetic acid (2 mmol) was added to the reaction mixture at the same temperature. Then, water (100 ml) was added, and the resulting suspension was treated with chloroform. The organic phase was dried over sodium sulfate, and the corresponding phenylethynylazine was isolated by column chromatography.
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