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quinoxaline - CAS 91-19-0

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Category
Main Product
Product Name
quinoxaline
Catalog Number
91-19-0
CAS Number
91-19-0
Molecular Weight
130.15
Molecular Formula
C8H6N2
COA
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MSDS
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Structure
CAS 91-19-0 quinoxaline
Specification
Purity
95%
Boiling Point
220-223ºC
Melting Point
29-34ºC
Density
1.124
Appearance
yellow solid
Storage
Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container.
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Reference Reading
1.Quinoxaline 1,4-di-N-Oxides: Biological Activities and Mechanisms of Actions.
Cheng G1, Sa W2, Cao C2, Guo L2, Hao H1, Liu Z3, Wang X1, Yuan Z4. Front Pharmacol. 2016 Mar 21;7:64. doi: 10.3389/fphar.2016.00064. eCollection 2016.
Quinoxaline 1,4-di-N-oxides (QdNOs) have manifold biological properties, including antimicrobial, antitumoral, antitrypanosomal and antiinflammatory/antioxidant activities. These diverse activities endow them broad applications and prospects in human and veterinary medicines. As QdNOs arouse widespread interest, the evaluation of their medicinal chemistry is still in progress. In the meantime, adverse effects have been reported in some of the QdNO derivatives. For example, genotoxicity and bacterial resistance have been found in QdNO antibacterial growth promoters, conferring urgent need for discovery of new QdNO drugs. However, the modes of actions of QdNOs are not fully understood, hindering the development and innovation of these promising compounds. Here, QdNOs are categorized based on the activities and usages, among which the antimicrobial activities are consist of antibacterial, antimycobacterial and anticandida activities, and the antiprotozoal activities include antitrypanosomal, antimalarial, antitrichomonas, and antiamoebic activities.
2.Hypervalent iodine(iii)-promoted N-incorporation into N-aryl vinylogous carbamates to quinoxaline diesters: access to 1,4,5,8-tetraazaphenanthrene.
Sagar A1, Vidaycharan S1, Shinde AH1, Sharada DS1. Org Biomol Chem. 2016 Apr 6. [Epub ahead of print]
A novel oxidative N-incorporation strategy for synthesis of quinoxaline diesters under metal-free conditions is described for the first time. The mild reaction conditions allow for this transformation via the formation of two C(sp2)-N bonds utilizing cheaply available NaN3 as the N-atom source. N-Aryl vinylogous carbamates in this study undergo azidation at enamino C(sp2)-H selectively. The robustness of this strategy is further demonstrated by the synthesis of a valuable 1,4,5,8-tetraazaphenanthrene derivative using a mild and convenient approach.
3.An efficient lactamisation/N-acyliminium Pictet-Spengler domino strategy for the diasteroselective synthesis of polyhydroxylated quinoxalinone, β-carboline and quinazolinone derivatives.
Subba Reddy BV1, Reddy BP2, Reddy PV3, Siriwardena A4. Org Biomol Chem. 2016 Apr 15. [Epub ahead of print]
A novel cascade strategy has been developed for the synthesis of polyhydroxylated tetrahydroindolo[1,2-a]pyrrolo[2,1-c]quinoxaline, tetrahydrodipyrrolo[1,2-a:2',1'-c]quinoxaline, hexahydro-1H-indolizino[8,7-b]indole, hexahydrobenzo[6,7]pyrrolo[1',2':1,2]azepino[3,4-b]indole, tetrahydrobenzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazoline, and tetrahydropyrrolo[1,2-a]tetrazolo[1,5-c]quinazoline scaffolds. The key step is a lactamisation/Pictet-Spengler condensation of a bifunctional sugar-derived hydroxy-γ-lactone component with an appropriate bifunctional aromatic amine component. This modular approach features the in situ-generation of a cyclic N-acyliminium intermediate that allows the diastereoselective assembly of these diverse polycyclic systems efficiently under mild and operationally simple conditions.
4.An exceptional 5:4 enantiomeric structure.
Wachter E1, Glazer EC1, Parkin S1, Brock CP1. Acta Crystallogr B Struct Sci Cryst Eng Mater. 2016 Apr 1;72(Pt 2):223-31. doi: 10.1107/S205252061600127X. Epub 2016 Apr 1.
The only crystals that could be grown from racemic solutions of the PF6(-) salt of the resolvable cation [Ru(2,9-dimethyl-1,10-phenanthroline)2(dipyrido[3,2-d:2',3'-f]quinoxaline)](2+) have translational symmetry only (space group P1), contain nine independent sets of ions, and include numerous independent solvent molecules (11 acetone, one diethyl ether and possibly several water molecules). Layers of hydrophobic cations alternate with layers containing most of the anions and solvent molecules. All nine cations have the same basic conformation, which is distorted by the presence of the methyl substituents on the two 1,10-phenanthroline ligands. Four pairs of enantiomeric cations within a layer are related by approximate inversion centers; the ninth cation, which shows no sign of disorder, makes the layer chiral. Within the cation layers stripes parallel to [110] of six cations alternate with stripes of three; the local symmetry and the cation orientations are different in the two stripes.
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