title: TMP-magnesium and TMP-zinc bases for the regioselective metalation of the cinnoline scaffold.
abstract: 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 TMP2Mg·2LiCl or the in situ generated base TMP2Zn·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.
authors: Department of Chemistry, Ludwig-Maximilians-University , Munich, Germany.
authors: Thomas
authors: T
authors: Klatt
authors: Daniela Sustac
authors: DS
authors: Roman
authors: Thierry
authors: T
authors: León
authors: Paul
authors: P
authors: Knochel
mesh_terms: D000468:Alkalies; D020650:Combinatorial Chemistry Techniques; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013938:Thymidine Monophosphate / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
chemical_list: D000468:Alkalies; D006574:Heterocyclic Compounds, 2-Ring; D013938:Thymidine Monophosphate; D008274:Magnesium; D015032:Zinc; C476282:cinnoline