Unexpectedly cyclized products by reaction of N-tosyliminoisoquinolinium ylides with trimethylsilylketene

Tetrahedron Letters

Volumn 48, Issue 39, 2007, Pages 7019-7021

  Kobayashi, Mayumi ^a   Kondo, Kazuhiro ^a   Aoyama, Toyohiko ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; KETENE DERIVATIVE; N TOSYLIMINOISOQUINOLINIUM YLIDE DERIVATIVE; PYRAZOLO[5,1 A]ISOQUINOLINE DERIVATIVE; REAGENT; TRIMETHYLSILYLKETENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; DEOXYGENATION;

EID: 34548224754     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.106     Document Type: Article

References (29)

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23. 3N were as follows: 2b (y. 40%), 2c (52%), 2d (55%), 2f (23%).
24. 4 was not efficient, although the efficiency for the synthesis of 2a was similar to our method (Scheme 2).
25. For a recent example of the 1,3-dipolar cyclization of N-ylides, see:. Fang X., Wu Y.-M., Deng J., and Wang S.-W. Tetrahedron 60 (2004) 5487-5493 and references cited therein
26. 2O, was observed by LC-MS.
27. The N-p-tosyliminoisoquinolinium ylides 1a-g were easily prepared by the standard tosylation of 6.{A figure is presented}
28. 3N (0.07 mL, 0.50 mmol) and trimethylsilylketene (0.45 mL, 0.20 mmol, 0.45 M in toluene solution) in toluene (2.0 mL) was refluxed for 24 h, allowed to cool, and directly concentrated. The residue was purified by silica gel column chromatography (hexanes-EtOAc, 7:1) to afford pyrazolo[5,1-a]isoquinoline (2a) (17.9 mg, 63%).
29. +).