420846-52-2

Upstream product

• 191999-28-7 (Z)-3-(4-bromobenzylidene)isobenzofuran-1(3H)-one 
• 1190831-57-2 (Z)-N-amino-3-(4-bromobenzylidene)isoindolin-1-one 
• 33757-48-1 N-quinolin-8-yl-benzamide 
• 98-88-4 benzoyl chloride 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 85-44-9 phthalic anhydride 
• 88-67-5 2-Iodobenzoic acid 
• 118520-70-0 1-copper(I) (4-bromophenyl)ethyne 
• 3979-66-6 3-(4-bromobenzylidene)isobenzofuran-1-(3H)-one 

Downstream Products

• 1062290-24-7 C₁₉H₁₄N₂O₂ 

Relevant academic research and scientific papers

The facile construction of the phthalazin-1(2H)-one scaffold via copper-mediated C-H(sp2)/C-H(sp) coupling under mild conditions

A novel strategy for the construction of the phthalazin-1(2H)-one scaffold has been developed by means of a copper-mediated cascade C-H/C-H coupling and intramolecular annulations and a subsequent facile hydrazinolysis. This C-H activation transformation proceeds smoothly with wide generality, good functional tolerance and high stereo- And regioselectivity under mild conditions. Through the removal of the directing group, the resulting moiety could easily be transformed into the phthalazin-1(2H)-one scaffold, which is known to be a privileged moiety and a bioactive nucleus in pharmaceuticals.

Base-catalyzed intramolecular heterocyclization of o-alkynylbenzhydrazides

The reaction of methyl o-(2-R-ethynyl)benzoates with hydrazine affords either fused 4-R-methylphthalazin-1-ones or 2-amino-3-R-methylideneisoindolin-1- ones. The latter are on treatment with KOH undergo recyclization into the corresponding 4-R-methylphthalazin- 1-ones.

Tuning selectivity of anionic cyclizations: Competition between 5-exo and 6-endo-dig closures of hydrazides of o-acetylenyl benzoic acids and based-catalyzed fragmentation/recyclization of the initial 5-exo-dig products

(Chemical Equation Presented) Depending on the reaction conditions and the nature of substituents at the triple bond, anionic cyclizations of hydrazides of o-acetylenyl benzoic acids can be selectively directed along three alternative paths, each of which

PHTHALAZINONE DERIVATIVES

A compound of the formula (I) wherein: A and B together represent an optionally substituted, fused aromatic ring or an optionally substituted, fused cyclohexene ring; D is selected from: (i), where Y1 is selected from CH and N, Y2 is selected from CH and N, Y3 is selected from CH, CF and N and Y4 is selected from CH and N; (ii) where Y1is selected from CH and N and Y2 is selected from CH and N; (iii) and where Q is O or S; and (iv), where Q is O or S; and RD is an optionally substituted C5-20 aryl group, bound to D by a carbon-carbon bond.