A novel strategy for the synthesis of 2-arylpyridines using one-pot 6π-azaelectrocyclization

Tetrahedron Letters

Volumn 49, Issue 28, 2008, Pages 4349-4351

  Kobayashi, Toyoharu ^a   Hatano, Sho ^a   Tsuchikawa, Hiroshi ^a   Katsumura, Shigeo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

Aromatization; Azaelectrocyclization; One pot; Pyridine; Synthesis

Indexed keywords

2 PYRIDINE DERIVATIVE; METHANE; PYRIDINE; PYRIDINE DERIVATIVE; SULFONAMIDE; VINYL DERIVATIVE;

AROMATIZATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; ONE POT SYNTHESIS; ROOM TEMPERATURE; THIN LAYER CHROMATOGRAPHY;

EID: 44649178242     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.048     Document Type: Article

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35. 3, 100 MHz) δ 165.3, 158.4, 150.4, 138.6, 138.5, 129.4, 128.8, 127.0, 121.1, 119.7, 61.8, 14.2.
36. All vinylstannanes were prepared by the coupling between the corresponding aryl halides and trans-1,2-bis(tributylstannyl)-ethene.
37. 4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the desired pyridine compounds.
38. 3, 100 MHz) δ 164.9, 152.4, 149.5, 140.2, 138.1, 137.4, 137.0, 133.6, 130.2, 128.7, 127.0, 125.7, 125.3, 124.5, 122.2, 121.5, 116.2, 115.7, 61.9, 14.2.
39. The generation of dienal 14 was confirmed by comparing with the one, which was obtained from the Stille coupling between vinylstannane 7 and the corresponding alcohol of 6 followed by oxidation, in a stepwise route. If the imine formation from 6 took place prior to the Stille coupling, the dienal 14 should not be observed.