Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 7, Issue 2, Pages 306-313Publisher
WILEY-BLACKWELL
DOI: 10.1002/asia.201100834
Keywords
alkynes; cyclization; isoquinolines; ketimines; nickel
Categories
Funding
- National Science Council of the Republic of China [NSC-99-2119-M-007-010]
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A convenient method for the synthesis of highly substituted isoquinolines and isoquinolinium salts by the nickel-catalyzed cyclization of ortho-haloketoximes and -ketimines, respectively, with alkynes is described. The reaction of ortho-haloketoximes and various alkynes in the presence of [Ni(PPh3)2Br2] and zinc powder in a mixture of acetonitrile and tetrahydrofuran at 80 degrees C for 15 hours gave 1,3,4-trisubstituted isoquinoline products in moderate to excellent yields and high regioselectivity. The corresponding isoquinoline N-oxide was found to be the intermediate in the cyclization reaction pathway. In contrast, the reaction of ortho-haloketimines and alkynes under similar catalytic conditions in tetrahydrofuran at 70 degrees C for two hours gave 1,2,3,4-tetrasubstituted isoquinolinium salts in good to excellent yields.
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