Studying the reactivity of (phthalazin-1(2 H)-on-2-yl)methyl trichloroacetimidate towards different C- and O-nucleophiles

Studying the reactivity of (phthalazin-1(2 H)-on-2-yl)methyl trichloroacetimidate towards different C- and O-nucleophiles

A simple and efficient synthesis of phthalazin-1(2 H)-one 2-substituted derivatives is achieved in very good yields via reaction of a phthalazinone–trichloroacetimidate with various C- and O-nucleophiles such as aromatic, heteroaromatic and olefinic reagents, sugars and cholesterol in CH 2Cl 2 in th...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 50; no. 48; pp. 6646 - 6650
Main Authors: El Nezhawy, Ahmed O.H., Gaballah, Samir T., Radwan, Mohamed A.A.
Format: Journal Article
Language:English
Published: Elsevier Ltd 02-12-2009
Subjects:
C-Nucleophiles
N-Phthalazinone
O-Nucleophiles
Trichloroacetimidate
Trimethylsilyl trifluoromethanesulfonate (TMSOTf)
O-Nucleophiles
Trichloroacetimidate
Trimethylsilyl trifluoromethanesulfonate (TMSOTf)
N-Phthalazinone
C-Nucleophiles
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Summary:A simple and efficient synthesis of phthalazin-1(2 H)-one 2-substituted derivatives is achieved in very good yields via reaction of a phthalazinone–trichloroacetimidate with various C- and O-nucleophiles such as aromatic, heteroaromatic and olefinic reagents, sugars and cholesterol in CH 2Cl 2 in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.09.068