Application of organolithium and related reagents in synthesis. Part 22. Synthetic strategies based on ortho-aromatic metallation. A concise regiospecific conversion of benzoic acids into the 4-pyridyl-2H-phthalazin-1-ones.

Authors
Brzezinski, JZ Epsztajn, J Bakalarz, AD Lajszczak, A Malinowski, Z
Citation
Jz. Brzezinski et al., Application of organolithium and related reagents in synthesis. Part 22. Synthetic strategies based on ortho-aromatic metallation. A concise regiospecific conversion of benzoic acids into the 4-pyridyl-2H-phthalazin-1-ones., SYN COMMUN, 29(3), 1999, pp. 457-473
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
3
Year of publication
1999
Pages
457 - 473
Database
ISI
SICI code
0039-7911(1999)29:3<457:AOOARR>2.0.ZU;2-J
Abstract
The synthesis of phthalazin-1-ones 6, 7, 8 via the reaction of 3-hydroxyiso indolin-1-ones 3, 4, 5 with hydrazine hydrate is described. Starting compou nds 3, 4, 5 were regiospecifically prepared upon the lithiation (n-BuLi) of the benzanilides 1 and subsequently the reaction of the dilithiated anilid es 2 with methyl pyridinecarboxylates.