82453-35-8Relevant articles and documents
SOME REACTIONS OF 3-HALOGENOCINNOLINES CATALYSED BY PALLADIUM COMPOUNDS
Ames, D. E.,Bull, D.
, p. 383 - 387 (2007/10/02)
3-Bromo-or 3-iodo-cinnoline (and 4-substituted analogues ) are condensed with terminal alkynes in the presence of Pd and Cu compounds as catalysts to give the 3-alkynyl-derivatives.When 4-chloro- or 4-phenoxy-compounds are used, the products react with amines, in the presence of copper(I) iodide, to form pyrrolocinnolines and with hydrazines to give either the same ring system or a pyrazolocinnoline.Hydrolysis of 3-alkynyl-4phenoxycinnoline to 3-alkynyl-4(1H)-cinnolinone, followed by cyclisation, yields the furocinnoline.Attempts to condense 3-halogenocinnolines with alkenes gave variable results: 3-phenyl ethenyl- and 3(2-pyridylethenyl)-4-(1H)-cinnolinones were obtained but 3-bromocinnoline gave the 3,3'-bicinnolinyl.Action of palladium acetate in the presence of ethyl acrylate converted 3-bromo-4-phenoxycinnoline into benzofurocinnoline and 3-bromo-4-phenylaminocinnoline into indolocinnoline.
