New and efficient RCM in pyridinic series: synthesis of 2H-dihydropyrano- or 2,3H-dihydrooxepino[3,2-b]pyridines

Tetrahedron Letters

Volumn 47, Issue 35, 2006, Pages 6235-6238

  Banaszak, Estelle ^a   Comoy, Corinne ^a   Fort, Yves ^a  

^a NANCY UNIVERSITÉ   (France)

Author keywords

2,3H dihydrooxepino 3,2 b pyridine; 2H dihydropyrano 3,2 b pyridine; RCM reaction; Stille cross coupling

Indexed keywords

2,3H DIHYDROOXEPINO[3,2 B]PYRIDINE DERIVATIVE; 2H DIHYDROPYRANO [3,2 B]PYRIDINE DERIVATIVE; BENZENE; HETEROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON; PYRIDINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 33746277539     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.139     Document Type: Article

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32. +, 63), 146 (45), 120 (100), 92 (86), 79 (28), 65 (60); IR (NaCl) ν 3020, 1578, 1442, 784.
33. Preparation of 2H-dihydropyrano[3,2-b]pyridine 1. Grubb's second generation catalyst (10 mol %) was added to a degassed solution of 3-allyloxy-2-vinylpyridine 7 (0.161 g, 1 mmol) dissolved in degassed and anhydrous toluene (20 mL). The reaction mixture was then heated at 70 °C for 24 h under a nitrogen atmosphere. After removal of the solvent under reduced pressure, the residue was purified by column chromatography on a silica gel (0.063-0.200 mm, eluent: hexane/AcOEt 70:30) which yielded 2H-pyrano[3,2-b]pyridine 1 (97 mg, 73%) as an orange oil. The spectroscopic data are in conformity with literature data (Ref. 2).
34. +]: 148.0776.