2-Quinoxalinecarbonitrile, 3-phenyl-, 1,4-dioxide

Base Information

• Chemical Name: 2-Quinoxalinecarbonitrile, 3-phenyl-, 1,4-dioxide
• CAS No.: 33074-70-3
• Molecular Formula: C15H9N3O2
• Molecular Weight: 263.255
• ChEMBL ID: CHEMBL460703
• DSSTox Substance ID: DTXSID30468912
• NSC Number: 725537
• Wikidata: Q82296404
• Mol file: 33074-70-3.mol

Synonyms:2-Quinoxalinecarbonitrile, 3-phenyl-, 1,4-dioxide;33074-70-3;CHEMBL460703;SCHEMBL18597959;DTXSID30468912;NSC725537;NSC-725537;1,4-di-N-oxide-2-cyano-3-phenylquinoxaline;1,4-dioxido-3-phenyl-quinoxaline-1,4-diium-2-carbonitrile

Chemical Property of 2-Quinoxalinecarbonitrile, 3-phenyl-, 1,4-dioxide

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 263.069476538
• Heavy Atom Count: 20
• Complexity: 485

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C([N+](=O)C3=CC=CC=C3N2[O-])C#N

Technology Process of 2-Quinoxalinecarbonitrile, 3-phenyl-, 1,4-dioxide

There total 7 articles about 2-Quinoxalinecarbonitrile, 3-phenyl-, 1,4-dioxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 46.5%

benzofurazan oxide (480-96-6,68100-26-5) + Benzoylacetonitrile (614-16-4) → 3-phenylquinoxaline-2-carbonitrile 1,4-dioxide (33074-70-3)

Guidance literature:

With potassium carbonate; In ethanol; at 20 ℃; for 3h;

DOI:10.3390/molecules17089683

Reference yield: 31.0%

3-phenyl-2-quinoxalinecarbonitrile (59393-45-2) → 3-phenylquinoxaline-2-carbonitrile 1,4-dioxide (33074-70-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; at 80 ℃; for 48h;

DOI:10.1021/acs.orglett.9b03590

Reference yield:

[(tert-pentyloxy)methyl]benzene (27674-74-4) → 3-phenylquinoxaline-2-carbonitrile 1,4-dioxide (33074-70-3)

Guidance literature:

Multi-step reaction with 3 steps

1: silver trifluoromethanesulfonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 80 °C / Inert atmosphere

2: sodium acetate; acetic acid / 0.25 h / 120 °C

3: 3-chloro-benzenecarboperoxoic acid / 1,2-dichloro-ethane / 48 h / 80 °C

With sodium acetate; silver trifluoromethanesulfonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane; chlorobenzene;

DOI:10.1021/acs.orglett.9b03590

upstream raw materials:

benzofurazan oxide

Benzoylacetonitrile

benzoic acid ethyl ester

1,2-diamino-benzene

Downstream raw materials:

1,4-Dioxy-3-phenyl-quinoxaline-2-carboxylic acid

3-phenyl-2-quinoxalinecarbonitrile

Refernces

• 1、 Hu, Yunzhen,Xia, Qing,Shangguan, Shihao,Liu, Xiaowen,Hu, Yongzhou,Sheng, Rong. "Synthesis and biological evaluation of 3-aryl-quinoxaline-2- carbonitrile 1,4-Di-N-oxide derivatives as hypoxic selective anti-tumor agents". . p. 9683 - 9696. Retrieved 2012/11/13.
• 2、 Vicente, Esther,Lima, Lidia M.,Bongard, Emily,Charnaud, Sarah,Villar, Raquel,Solano, Beatriz,Burguete, Asuncion,Perez-Silanes, Silvia,Aldana, Ignacio,Vivas, Livia,Monge, Antonio. "Synthesis and structure-activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents". . p. 1903 - 1910. Retrieved 2008/12/22.