94797-68-9

Upstream product

• 36041-39-1 2-benzoyl-1,4-benzoquinone 
• 134-81-6 benzil 
• 113674-51-4 2-Carbobenzoxybenzaldehyde 
• 768-03-6 Phenyl vinyl ketone 
• 6125-26-4 phenyl(2-phenyl-2,3-dihydrobenzo[d]thiazol-2-yl)methanone 
• 130-15-4 [1,4]naphthoquinone 
• 100-52-7 benzaldehyde 
• 94797-63-4 4a,8a-cis-4a,5-trans-5-acetoxy-4a-benzoyl-4a,5,8,8a-tetrahydro-1,4-naphthoquinone 

Downstream Products

• 74652-31-6 2-benzoylnaphthalene-1,4-dione 
• 97971-68-1 (3-benzoyl-1,4-dihydroxy-2-naphthyl)(phenyl)methanone 

Relevant academic research and scientific papers

N-Heterocyclic carbene based catalytic platform for Hauser-Kraus annulations

The venerable Hauser-Kraus annulation is an effective and convergent method for generating oxygenated polycyclic aromatic compounds. Despite its application in complex molecule synthesis, the harsh and strongly basic conditions can limit its utility in more functionalized molecular settings. We have developed the first catalytic Hauser-Kraus annulation based on N-heterocyclic carbene catalysis that proceeds under milder conditions. We demonstrate the scope of the transformation in the presence of several functional groups. We also propose a concerted mechanism for the annulation that proceeds through a non-canonical Breslow intermediate. This journal is

Radical hydroalkylation and hydroacylation of alkenes by the use of benzothiazoline under thermal conditions

The hydroalkylation and hydroacylation of electrondeficient alkenes proceeded smoothly by using benzothiazoline derivatives as radical-transfer reagents under thermal conditions without light irradiation or any additive. Both benzyl and benzoyl moieties were transferred efficiently.

Benzothiazolines as radical transfer reagents: Hydroalkylation and hydroacylation of alkenes by radical generation under photoirradiation conditions

Novel radical transfer reagents under photoirradiation conditions were developed by the use of benzothiazoline derivatives. These reagents enabled both hydroalkylation and hydroacylation of alkenes under neutral conditions at ambient temperature without a

The cytotoxic effect of 2-acylated-1,4-naphthohydroquinones on leukemia/lymphoma cells

Here, we tested seven 2-acylated-1,4-hydronaphthoquinones for their cytotoxic effects on a panel of cancer lymphoma/leukemia cells and compared to a non-cancer origin cell line. Several naphthohydroquinones exhibited selective cytotoxic effects on lymphom

Green photochemistry: Photo-Friedel-Crafts acylations of 1,4-naphthoquinone in room temperature ionic liquids

The photo-Friedel-Crafts acylation of 1,4-naphthoquinone with various aldehydes was investigated in a series of room temperature ionic liquids. High conversions and selectivities were achieved in [C2mim] +-based ionic liquids with the highest isolated yields found in [C2mim][NTf2]. The developed procedure allowed for a replacement of hazardous solvents such as benzene and acetonitrile which are commonly used for this transformation. The Royal Society of Chemistry 2009.

The "photo-Friedel-Crafts acylation" of 1,4-naphthoquinones

The photochemical reaction between 1,4-naphthoquinone (3) and several aliphatic and aromatic aldehydes 5a-f resulted in the formation of acylated naphthohydroquinones 6a-f in moderate to good yields of 42-79%. When benzaldehyde was used, the dibenzoylated product 7 was also isolated, in 14% yield. The regioselectivity was studied with the unsymmetrical substituted naphthoquinone 4 and butyraldehyde 5b and benzaldehyde 5f. With 5f, the corresponding diaroylated compound 12 was again isolated as a minor product. Oxidation of selected photoproducts afforded the corresponding acylated naphthoquinones 8a, 8b, 8f, and 13 in moderate to excellent yields of 53-94%. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

An improved method for the preparation of 4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates from 2-acyl-1,4-benzoquinones and mercaptoacetates

4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates (4) have been synthesized in a one-pot procedure from 2-acyl-1,4-benzoquinones (1) and mercaptoacetates (2) by using 1-trimethylsilylimidazole as a protective reagent as well as a base. Thus, reaction of 1 with 2 in THF at room temperature was followed by treatment with excess of 1-trimethylsilylimidazole at 80°C. Then the cooled mixture was hydrolyzed with hydrochloric acid and oxidized with cerium(IV) ammonium nitrate (CAN) to give the expected thiophenequinone derivatives (4). 4,9-Dioxo-4,9-dihydronaphtho[2,3-b]thiophene-2-carboxylates (7) were similarly prepared from 2-acyl-1,4-naphthoquinones (5) and mercaptoacetates, in general, by omitting the CAN oxidation procedure.

Acyl Rearrangements in Acylbenzoquinone Cycloadducts

A number of cycloadducts between 2-acetyl- and 2-benzoyl-1,4-benzoquinones and dienes have been prepared and the direction of the substituent acyl group migration has been shown to depend on the diene substituents.The initial adducts from 2-acetylnaphthoquinone and dienes either epimerised or yielded 9,10-anthraquinone on attempted rearrangement.