52966-67-3Relevant academic research and scientific papers
4-Substituted 5-nitroisoquinolin-1-ones from intramolecular Pd-catalysed reaction of N-(2-alkenyl)-2-halo-3-nitrobenzamides
Dhami, Archana,Mahon, Mary F.,Lloyd, Matthew D.,Threadgill, Michael D.
experimental part, p. 4751 - 4765 (2009/10/23)
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-nitrobenzamide similarly gave 2-benzhydryl-4-benzyl-5-nitroisoquinolin-1-one and 2-benzhydryl-4-benzylidene-5-nitro-3,4-dihydroisoquinolin-1-one. The isomeric products are not interconvertible. A deuterium-labelling study indicated that the isomers were formed by different pathways: a π-allyl-Pd route and the classical Heck route. The corresponding secondary amides N-allyl-2-iodo-3-nitrobenzamide and N-((substituted)-cinnamyl)-2-iodo-3-nitrobenzamide gave good yields of the required 4-methyl- and 4-((substituted)-benzyl)-5-nitroisoquinolin-1-ones, respectively, under optimised conditions (Pd(PPh3)4, Et3N, Bu4NCl, 150 °C, rapid heating). Hydrogenation of the nitro groups gave 4-methyl- and 4-benzyl-5-aminoisoquinolin-1-ones, which were potent inhibitors of PARP-1 activity.
A CONVENIENT SYNTHESIS OF N-ALKYL AND N,N-DIALKYLTRIFLUOROACETAMIDES IN A SOLID-LIQUID TWO-PHASE SYSTEM IN THE PRESENCE OF PHASE-TRANSFER CATALYSTS
Landini, Dario,Penso, Michele
, p. 791 - 800 (2007/10/02)
Trifluoroacetamide is easily monoalkylated in a K2CO3-organic solvent solid-liquid two-phase system affording in good to excellent yields N-alkyltrifluoroacetamides.Under the same conditions, the latter, in turn, ract with alkylating agents giving N,N-dialkyltrifluoroacetamides in high yields.
