Novel construction of hydro-2-benzazepines based on 7-endo selective Friedel-Crafts-type reaction of vinyloxiranes

Tetrahedron Letters

Volumn 48, Issue 48, 2007, Pages 8558-8561

  Nagumo, Shinji ^a   Mizukami, Megumi ^b   Wada, Koji ^b   Miura, Toshie ^b   Bando, Hideo ^b   Kawahara, Norio ^b   Hashimoto, Yasunori ^a   Miyashita, Masaaki ^a   Akita, Hiroyuki ^c  

^a KOGAKUIN UNIVERSITY   (Japan)

^b HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

^c TOHO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; BENZAZEPINE DERIVATIVE; GALANTAMINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; FRAGMENTATION REACTION; FRIEDEL CRAFTS REACTION; STEREOSPECIFICITY; SYNTHESIS;

EID: 35548997784     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.106     Document Type: Article

References (14)

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6. 3. For the synthesis of 4-benzyltosylamino-2,3-epoxy-butan-1-ol, see:. Adams C.E., Walker F.J., and Sharpless K.B. J. Org. Chem. 50 (1985) 420 Syntheses of 3b-d were also carried out according to the above method
7. 3).
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11. Nucleophilicity of the aromatic ring in 3c is higher than that of the aromatic ring in 3b. Sha C.-K., Young J.-J., Yeh C.-P., Chang S.-C., and Wang S.-L. J. Org. Chem. 56 (1991) 2694
12. 4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with hexane/AcOEt (3/2) to give 4c (464 mg, 1.01 mmol, 91%).
13. The 4c/5c ratios were 1:2.1 (1 min), 1:1 (10 min), 1.8:1 (20 min), 2.5:1 (30 min), 5.8:1 (1 h), 17.5:1 (2 h) and 31:1 (3 h).
14. A part of 3c may be transformed into 4c via a direct cyclization (Scheme 2, path a).