Tetrahedron

4-Substituted 5-nitroisoquinolin-1-ones from intramolecular Pd-catalysed reaction of N-(2-alkenyl)-2-halo-3-nitrobenzamides

A Dhami, MF Mahon, MD Lloyd, MD Threadgill

Index: Dhami, Archana; Mahon, Mary F.; Lloyd, Matthew D.; Threadgill, Michael D. Tetrahedron, 2009 , vol. 65, # 24 p. 4751 - 4765

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Citation Number: 13

Abstract

4-Methyl-and 4-benzyl-5-aminoisoquinolin-1-ones are close analogues of the water-soluble PARP-1 inhibitor 5-AIQ. Their synthesis was approached through Pd-catalysed cyclisations of N-(2-alkenyl)-2-iodo-3-nitrobenzamides. Reaction of N, N-diallyl-2-iodo-3-nitrobenzamide with Pd (PPh3) 4 gave a mixture of 2-allyl-4-methyl-5-nitroisoquinolin-1-one and 2-allyl-4- methylene-5-nitro-3, 4-dihydroisoquinolin-1-one. N-Benzhydryl-N-cinnamyl-2-iodo-3- ...