73079-06-8

Upstream product

• 84-65-1 9,10-phenanthrenequinone 
• 1560-32-3 10-bromo-10H-anthracen-9-one 
• 104-94-9 4-methoxy-aniline 
• 2101-87-3 p-methoxy-phenylazide 
• 73079-05-7 C₂₈H₂₁N₃O₂ 
• 14343-92-1 benzylideneanthrone 
• 90-44-8 anthracen-9(10H)-one 

Downstream Products

• 96069-40-8 10-(4-Methoxy-phenylimino)-9-phenyl-9,10-dihydro-[9]anthrol 

Relevant academic research and scientific papers

Phenylimino-10H-anthracen-9-ones as novel antimicrotubule agents - Synthesis, antiproliferative activity and inhibition of tubulin polymerization

A novel series of phenylimino-10H-anthracen-9-ones and 9-(phenylhydrazone)- 9,10-anthracenediones were synthesized and evaluated for interaction with tubulin and for cytotoxicity against a panel of human tumor cell lines. The 10-(3-hydroxy-4-methoxy-pheny

REACTIONS OF IMINODIMAGNESIUM REAGENTS WITH 1,4-QUINONES: THEIR STRUCTURAL FACTORS GOVERNING THE MODES OF REACTIONS

Reactions of benzo-, naphtho- and anthraquinone derivatives (unsubstituted and substituted) with aryliminodimagnesium and aryloxymagnesium of a weak electron-donating ability were studied.In addition to the reduction products (quinhydrones and hydroquinones), nuclear substitution and condensation (with =C=O) products were formed.The efficiency of single electron transfer (SET) from ArN(MgBr)2, evaluated by the relative values of the difference between the oxidation and reduction potentials of the reactants (ΔE=Eox-Ered), varies with the electron-accepting power of quinones. ΔE governs the modes of semiquinone appearance (ESR signals) and the relative amounts of the heat of reactions, reflecting the types and yields of the products.It is concluded that condensation products of both components are produced in the reactions of quinones with the lower SET efficiency by the presence of a fused benzene ring or MeO substituent.The structure-reactivity relationship proposed previously for reactions of various magnesium reagents is extended in the reactions with a variety of quinones even in cases of higher SET efficiency.

Syntheses and Reactions of Spiroanthronetriazolines

Quinone methide 1a reacts with aryl azides 2 to give the corresponding spiroanthronetriazolines 3 along with byproducts, collected in Table I, which are formed by the thermal reaction of 3 or 1a.Quinone methide 1b adds to azides 2 to give spiroanthronetriazolines 5 or their subsequent products.Pyrolysis of 3 regenerates the starting quinone methide 1a and azide 2, and their photolysis leads to 1a.Pyrolysis and photolysis of 5 yield aryliminoanthrone 7, arylaminodibenzocycloheptenone 12, or its isomer 19.Attempts to convert 3 and 5 into spiroanthroneaziridines 14 and 15, respectively, were unsuccessful.Reactions of 3 and 5 with acid catalysts give the rearrangement products dibenzocycloheptenediones 23 and 24, respectively, in high yields.These reactions are discussed in mechanistic terms.