Furo[3,4-b]quinoline-1,3-dione

Base Information

• Chemical Name: Furo[3,4-b]quinoline-1,3-dione
• CAS No.: 4945-42-0
• Molecular Formula: C11H5 N O3
• Molecular Weight: 199.166
• DSSTox Substance ID: DTXSID40401951
• Wikidata: Q82205275
• Mol file: 4945-42-0.mol

Synonyms:furo[3,4-b]quinoline-1,3-dione;4945-42-0;2,3-quinolinedicarboxylic anhydride;SCHEMBL310881;DTXSID40401951;NLVZUORLSQCGFQ-UHFFFAOYSA-N;AKOS000295037;2,3-quinolinedicarboxylic acid anhydride;1H,3H-FURO[3,4-B]QUINOLINE-1,3-DIONE

Chemical Property of Furo[3,4-b]quinoline-1,3-dione

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 199.026943022
• Heavy Atom Count: 15
• Complexity: 315

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C3C(=N2)C(=O)OC3=O

Technology Process of Furo[3,4-b]quinoline-1,3-dione

There total 1 articles about Furo[3,4-b]quinoline-1,3-dione 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: 51.0%

quinoline-2,3-dicarboxylic acid (643-38-9) → quinoline-2,3-dicarboxylic acid anhydride (4945-42-0)

Guidance literature:

With acetic anhydride; for 1.5h; Reflux;

DOI:10.1016/j.tet.2010.03.100

Reference yield: 70.0%

quinoline-2,3-dicarboxylic acid anhydride (4945-42-0) + 4-methoxy-benzylamine (2393-23-9) → 2-(4-methoxybenzyl)-2H-pyrrolo[3,4-b]quinoline-1,3-dione (929206-53-1)

Guidance literature:

quinoline-2,3-dicarboxylic acid anhydride; 4-methoxy-benzylamine; In tetrahydrofuran; at 20 ℃; for 2h;

With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; for 12h; Heating;

DOI:10.1021/jo062077x

Reference yield:

quinoline-2,3-dicarboxylic acid anhydride (4945-42-0) → 3-hydroxy-2,3-dihydro-2-(4-methoxybenzyl)-pyrrolo[3,4-b]quinolin-1-one (929206-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 2 h / 20 °C

1.2: 70 percent / DCC; DMAP / tetrahydrofuran / 12 h / Heating

2.1: 77 percent / NaBH₄; Mg(ClO₄)2 / tetrahydrofuran; CHCl₃ / 0.33 h / 0 °C

With sodium tetrahydroborate; magnesium(II) perchlorate; In tetrahydrofuran; chloroform;

DOI:10.1021/jo062077x

upstream raw materials:

quinoline-2,3-dicarboxylic acid

Downstream raw materials:

quinoline-2,3-dicarboxylic acid-dianilide

2-(4-methoxybenzyl)-2H-pyrrolo[3,4-b]quinoline-1,3-dione

3-hydroxy-2,3-dihydro-2-(4-methoxybenzyl)-pyrrolo[3,4-b]quinolin-1-one

3-acetoxy-2,3-dihydro-2-(4-methoxybenzyl)-1H-pyrrolo[3,4-b]quinolin-1-one

Refernces