6,11-Dioxo-12-naphtho[2,3-b]indolizinecarboxylic acid ethyl ester

Base Information

• Chemical Name: 6,11-Dioxo-12-naphtho[2,3-b]indolizinecarboxylic acid ethyl ester
• CAS No.: 3306-93-2
• Molecular Formula: C19H13NO4
• Molecular Weight: 319.317
• NSC Number: 119236
• DSSTox Substance ID: DTXSID10297924
• Nikkaji Number: J1.010.993K
• Wikidata: Q27165743
• Pharos Ligand ID: VSSA5F5TWPU3
• ChEMBL ID: CHEMBL458765
• Mol file: 3306-93-2.mol

Synonyms:3306-93-2;ethyl 6,11-dioxo-6,11-dihydrobenzo[f]pyrido[1,2-a]indole-12-carboxylate;NSC119236;NSC-119236;6,11-dioxo-12-naphtho[2,3-b]indolizinecarboxylic acid ethyl ester;ethyl 6,11-dioxonaphtho[2,3-b]indolizine-12-carboxylate;CHEMBL458765;1-Carboethoxy-2,3-phthaloylpyrrocoline;ChemDiv3_001941;NCIStruc1_001582;NCIStruc2_001066;Oprea1_010120;Oprea1_229435;CHEBI:93990;DTXSID10297924;HMS1478I05;BDBM50463924;CCG-36636;NCGC00014207;NCI119236;STK981928;AKOS001634473;IDI1_020907;NCGC00014207-02;NCGC00014207-03;NCGC00097316-01;NCI60_000459;A821700;AF-399/14738011;SR-01000081644;SR-01000081644-1;BRD-K28100108-001-01-0;Q27165743;ethyl 6,11-bis(oxidanylidene)naphtho[2,3-b]indolizine-12-carboxylate

Chemical Property of 6,11-Dioxo-12-naphtho[2,3-b]indolizinecarboxylic acid ethyl ester

Chemical Property:

• PSA: 64.85000
• Density: 1.37g/cm³
• LogP: 2.89140
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 319.08445790
• Heavy Atom Count: 24
• Complexity: 560

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C2C=CC=CN2C3=C1C(=O)C4=CC=CC=C4C3=O

Technology Process of 6,11-Dioxo-12-naphtho[2,3-b]indolizinecarboxylic acid ethyl ester

There total 15 articles about 6,11-Dioxo-12-naphtho[2,3-b]indolizinecarboxylic acid ethyl ester 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: 92.0%

pyridine (110-86-1) + acetylenedicarboxylic acid diethyl ester (762-21-0) + [1,4]naphthoquinone (130-15-4) → 6,11-dioxo-6,11-dihydro-benzo[f]pyrido[1,2-a]indole-12-carboxylic acid ethyl ester (3306-93-2)

Guidance literature:

With copper(II) chloride hydrate; oxygen; In N,N-dimethyl-formamide; at 180 ℃; for 16h; under 760.051 Torr;

DOI:10.1021/jo500456d

Reference yield: 91.0%

pyridine (110-86-1) + 2,3-Dichloro-1,4-naphthoquinone (117-80-6) + ethyl acetoacetate (141-97-9) → 6,11-dioxo-6,11-dihydro-benzo[f]pyrido[1,2-a]indole-12-carboxylic acid ethyl ester (3306-93-2)

Guidance literature:

In ethanol; for 6h; Reflux;

DOI:10.4067/S0717-97072012000200015

Reference yield: 91.0%

3-ethoxycarbonyltriazolo<1,5-a>pyridine (87838-54-8) + [1,4]naphthoquinone (130-15-4) → 6,11-dioxo-6,11-dihydro-benzo[f]pyrido[1,2-a]indole-12-carboxylic acid ethyl ester (3306-93-2)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; acetic acid; In 1,2-dichloro-benzene; at 120 ℃; for 24h; Reagent/catalyst; Temperature; Catalytic behavior; Mechanism; Sealed tube;

DOI:10.1002/adsc.202100965

upstream raw materials:

pyridine

2,3-Dichloro-1,4-naphthoquinone

ethyl phenylsulfenylacetate

ethyl acetoacetate

Downstream raw materials:

6,11-dioxo-6,11-dihydrobenzo[f]pyrido[1,2-a]indole-12-carboxylic acid

isopropyl 6,11-dioxo-6,11- dihydrobenzo[f]pyrido[1,2-a]indole-12-carboxylate

6,11-dioxo-6,11-dihydro-benzo[f]pyrido[1,2-a]indole-12-carboxylic acid anilide

1-Carbamoyl-2,3-phthaloyl-pyrrocolin

Refernces

• 1、 Rawat, Deepa,Adimurthy, Subbarayappa. "Transannulation of Pyridotriazoles with Naphthoquinones and Indoles: Synthesis of Benzo[f]Pyrido[1,2-a]Indoles and Indolizino[3,2-b]indoles". . p. 71 - 76. Retrieved 2021/10/29.
• 2、 Yang, Rui,Chen, Yu,Pan, Liangkun,Yang, Yanyan,Zheng, Qiang,Hu, Yue,Wang, Yuxi,Zhang, Liangren,Sun, Yang,Li, Zhongjun,Meng, Xiangbao. "Design, synthesis and structure-activity relationship study of novel naphthoindolizine and indolizinoquinoline-5,12-dione derivatives as IDO1 inhibitors". . p. 4886 - 4897. Retrieved 2018/09/11.