82453-00-7Relevant academic research and scientific papers
TMP-magnesium and TMP-Zinc bases for the regioselective metalation of the cinnoline scaffold
Klatt, Thomas,Roman, Daniela Sustac,Leon, Thierry,Knochel, Paul
supporting information, p. 1232 - 1235 (2014/03/21)
A regioselective functionalization of cinnolines in positions 3 and 8 using metalations has been developed. This involves either the use of a frustrated Lewis pair consisting of BF3·Et2O and TMP 2Mg·2LiCl or the in situ generated base TMP 2Zn·2MgCl2·2LiCl. Successive metalations allow the preparation of 3,8-disubstituted cinnolines. Various functionalizations by acylation, allylation, and cross-coupling reactions with aryl halides or alkenyl iodides were carried out successfully.
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.
