Application of a recyclable fluorous oxime in the convenient synthesis of 3-amino-1,2-benzisoxazoles and 4-amino-1H-2,3-benzoxazines
A microwave-assisted, fluorous synthetic route to 3-amino-1,2- benzisoxazoles and 4-amino-1H-2,3-benzoxazines has been developed. The strategy comprises linking the respective 2-fluorobenzonitrile or 2-(bromomethyl) benzonitrile to a fluorous oxime tag to give an aryloxime intermediate which then undergoes cyclization with concomitant cleavage of the substrate-tag in acidic conditions to provide the desired product in good to moderate yields. In addition, the aryloxime intermediate could be subjected to further reactions to expand the compound library. The product could be easily separated using fluorous solid-phase extraction (F-SPE) and the fluorous ketone recovered could be converted back to the fluorous oxime and reused in the next run of the synthesis.
HETEROARYLOXY-SUBSTITUTED PHENYLAMINOPYRIMIDINES AS RHO-KINASE INHIBITORS
The invention relates to heteroaryloxy-substituted phenylaminopyrimidines, to methods for the production thereof, and to the use of the same for producing medicaments for the treatment and/or prophylaxis of diseases, especially cardiovascular diseases. The inventive compounds inhibit Rho-kinase.
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Page/Page column 57-58
(2010/02/06)
Novel one-pot cyclization of ortho substituted benzonitriles to 3-amino-1,2-benzisoxazoles
A novel one-pot synthesis of 3-amino-1,2-benzisoxazoles (iii), from ortho substituted benzonitriles (i), is described. The synthesis likely involves a SNAr reaction of an activated ortho halo or nitro group by a hydroxamate anion, followed by an intra-mol
Palermo
p. 2885 - 2886
(2007/10/03)
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