Jeffery S. Hinkle, O. Lever
1988
Citations
0
Influential Citations
2
Citations
Journal
Tetrahedron
Abstract
Abstract A method for the synthesis of isoquinolines functionalized with differentiated nitrogen substituents at positions 3 and 4 is described. The method involves tosylarion of a 3-hydroxy-4-nitroisoquinoline and subsequent tosylate displacement by amine nucleophiles to give 3-amino-4-nitroisoquinolinc derivatives, the products of specific C-O bond cleavage. Reduction of the 4-nitro group and elaboration of the resulting 4-amino moiety provides the differentiated 3- and 4-amino functions, not readily available by other methods. Appropriately substituted compounds are amenable to further transformations, illustrated by their conversion to imidazo[5,4-c]isoquinoline derivatives. Additional studies on the tosylatc displacement indicated that thiol displacement also occurs by scission of. the CO bood to give a 3-thioether derivative, and that reactions of the 4-nitro-3-tosyloxyisoquinoline system with certain other nuclcophilcs, including alcohols, did not proceed readily.