3712-09-2

Basic information

• Product Name: BENZO(G)QUINOLINE-5,10-DIONE
• Synonyms: BENZO(G)QUINOLINE-5,10-DIONE;1-Azaanthraquinone;5,10-Dihydrobenzo[g]quinoline-5,10-dione
• CAS NO: 3712-09-2
• Molecular Formula: C13H7NO2
• Molecular Weight: 209.2002
• Mol File: 3712-09-2.mol

Chemical Properties

• Melting Point: 278-280 °C
• Boiling Point: 407°Cat760mmHg
• Flash Point: 202.1°C
• Appearance: /
• Density: 1.373g/cm³
• Vapor Pressure: 7.77E-07mmHg at 25°C
• Refractive Index: 1.668
• PKA: 0.47±0.20(Predicted)
• CAS DataBase Reference: BENZO(G)QUINOLINE-5,10-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZO(G)QUINOLINE-5,10-DIONE(3712-09-2)
• EPA Substance Registry System: BENZO(G)QUINOLINE-5,10-DIONE(3712-09-2)

Safety Data

• Hazardous Substances Data: 3712-09-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H7NO2/c15-12-8-4-1-2-5-9(8)13(16)11-10(12)6-3-7-14-11/h1-7H

Upstream product

• 3645-26-9 10-chlorobenzo[g]quinoline 
• 854046-82-5 5,10-dichloro-benzo[g]quinoline 
• 14706-92-4 [10,10']bi[benzo[g]quinolinyl] 
• 10470-83-4 5,8-quinolinedione 
• 10034-09-0 1-methoxy-1,3-butadiene 
• 1515-76-0 1-acetoxybuta-1,3-diene 
• 1515-76-0 1-acetoxy-1,3-butadiene 
• 15910-11-9 1,4-diacetoxy 1,3-butadiene 
• 63383-46-0 1-(trimethylsiloxy)-1,3-butadiene 
• 106-99-0 buta-1,3-diene 
• 18710-11-7 1,2,3,4-tetrahydro-benzo[g]quinoline-5,10-dione 
• 13785-27-8 6,9-dihydro-6,9-ethanobenzoquinoline 
• 135831-91-3 N-benzyl-1,2,3,4-tetrahydroquinolinequinone-5,8-dione 
• 1066-30-4 chromium(lll) acetate 

Relevant articles and documents

Azaanthraquinone assembly from N -propargylamino quinone via a Au(I)-catalyzed 6- endo - Dig cycloisomerization

A methodology to assemble the azaanthraquinone skeleton from N-propargylamino quinone by a Au(I)-catalyzed 6-endo-dig cycloisomerization was developed. The catalytic process was applied to the synthesis of alkaloid cleistopholine and its analogues. A mechanism involving benign nucleophilicity of the aminoquinone was proposed.

Copper bromide-catalyzed c-alkylation of 2-amino-1,4-naphthoquinone: New synthesis of 1-azaanthraquinones

Copper(I) bromide catalyzes the regioselective Michael addition reaction of 2-amino-1,4-naphthoquinone (5) with methyl vinyl ketone and 2-propenal to provide easy access to C-alkylated quinone derivatives, useful precursors of 1-azaanthraquinones.

Metallation of pyridines and quinolines in the presence of a remote carboxylate group. New syntheses of heterocyclic quinones

2-(3- and 2-Pyridylcarbonyl)benzoic acids (2,3), 2-(2-pyridylcarbonyl) thiophene-3-carboxylic acid (6), 2-(3-quinolylcarbonyl)benzoic acid (10), and most of the corresponding esters (compounds 1, 7 and 9) are readily synthesized and involved in a deprotonation-condensation sequence. Biologically active aza-anthraquinones such as benzo[g]isoquinoline-5,10-dione (2-azaanthraquinone, 4) and benzo[g]quinoline- 5,10-dione (1-azaanthraquinone, 5) are prepared using the strategy. Extension to other heterocyclic quinones such as thieno[3,2-g]quinoline-4,9-dione (8) and benzo[j]phenanthridine-7,12-dione (11) is also investigated.

Synthesis of Quinolinequinones and 1,2,3,4-Tetrahydroquinolinequinones via Cyclobutenediones

N-Benzyl-1,2,3,4-tetrahydrocyclobutapyridine-5,6-dione is easily synthesized and functions as a synthetic equivalent of the unstable pyridiocyclobutenedione.Regiospecific introduction of unsaturated nucleophiles at the more reactive carbonyl group, followed by thermolysis in xylene in vessels open to air, rapidly establishes the tetrahydroquinolinequinone system which can be oxidized to the corresponding quinolinequinone with 2,3-dichloro-5,6-dicyanoquinone.

Effect of Boron Trifluoride-Diethyl Ether (BF3*OEt2) in the Diels-Alder Reaction of Quinoline- and Isoquinoline-5,8-dione with Unsymmetrical Aliphatic Dienes: Theroretical Study on the Orientation of Cycloadditions

The Diels-Alder reaction of quinoline- and isoquinoline-5,8-dione with piperylene gave regioisomers of the substituted azaanthraquinones, while the Lewis acid catalyst boron trifluoride-diethyl ether showed a drastic effect on regioseletivity in the reactions with piperylene.The Frontier Molecular Orbital (FMO) theory (caculated by CNDO/2 method) was applied to explain the orientation of the catalysed regioselective cycloadditions, by considering secondary orbital interactions.

Cycloaddition Routes to Azaanthraquinone Derivatives. 1. Use of Azadienophiles

The mono- and diazanaphthoquinones underwent facile cycloaddition with cyclic and alicyclic dienes, and in the majority of these cycloadditions the initial 1:1-cycloadducts or their tautomers and intermediate products formed in the oxidation procedure leading to the final azaanthraquinones were isolated.Quinoline-5,8-dione and 1-methoxy-1,3-cyclohexadiene gave the 8-methoxy isomer in an essentially regiospecific cycloaddition; isoquinoline-5,8-dione, however, gave both the 5- and 8-methoxy isomers in a 2.8:1 ratio.These structural assignments were verified by alternative syntheses of the possible isomers using heteroatom-directed lithiation procedures.