129722-90-3

Basic information

• Product Name: Meridine
• Synonyms: Meridine;12-Hydroxy-7,9,13-triaza-8H-dibenz[a,de]anthracen-8-one;12-Hydroxy-8H-benzo[b]pyrido[4,3,2-de][1,7]phenanthroline-8-one
• CAS NO: 129722-90-3
• Molecular Formula: C18H9 N3 O2
• Molecular Weight: 299.283
• Mol File: 129722-90-3.mol

Chemical Properties

• Boiling Point: 633°Cat760mmHg
• Flash Point: 336.6°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 6.28E-16mmHg at 25°C
• Refractive Index: 1.834
• CAS DataBase Reference: Meridine(CAS DataBase Reference)
• NIST Chemistry Reference: Meridine(129722-90-3)
• EPA Substance Registry System: Meridine(129722-90-3)

Safety Data

• Hazardous Substances Data: 129722-90-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H9N3O2/c22-12-6-8-20-17-14(12)15-13-10(5-7-19-16(13)18(17)23)9-3-1-2-4-11(9)21-15/h1-8H,(H,20,22)

Upstream product

• 158398-83-5 meridine methyl ether 
• 187219-46-1 2,2-Dimethyl-5-[(4-oxo-4H-pyrido[2,3,4-kl]acridin-5-ylamino)-methylene]-[1,3]dioxane-4,6-dione 
• 1466-88-2 2-nitrocinnamic aldehyde 
• 115170-26-8 4-methoxy-5,8-quinolinedione 
• 283152-31-8 4-(2-nitrophenyl)-1-(dimethylamino)-1-aza-1,3-butadiene 
• 158398-82-4 4-methoxy-6-(2'-nitrophenyl)pyrido[3,2-g]quinoline-5,10-dione 
• 158398-81-3 1,4-dihydro-6-methoxy-4-(2'-nitrophenyl)pyrido[3,2-g]quinoline-5,10-dione 
• 191849-03-3 4-chloro-6-(2'-nitrophenyl)pyrido[3,2-g]-quinoline-5,10-dione 
• 212394-01-9 1,4-dihydro-6-chloro-4-(2'-nitrophenyl)pyrido[3,2-g]-quinoline-5,10-dione 
• 56741-29-8 2,5-dimethoxy-3-nitroaniline 
• 187219-36-9 5,8-dimethoxy-7-nitro-4-quinolone 
• 187219-35-8 5-[(2,5-Dimethoxy-3-nitro-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 187219-44-9 7-amino-5,8-dimethoxy-4-[2'-(tert-butoxycarbonylamino)phenyl]quinoline 
• 187219-45-0 7-[5-(2,2-dimethyl-4,6-dioxo-1,3-dioxanyliden)methylamino]-5,8-dimethoxy-4-[2'-(tert-butoxycarbonylamino)phenyl]quinoline 

Relevant articles and documents

Oxidative Cyclization of Kynuramine and Ynones Enabling Collective Syntheses of Pyridoacridine Alkaloids

A cerium(III)-catalyzed oxidative cyclization of kynuramine and ynones has been reported as a key reaction in the total synthesis of marine pentacyclic pyridoacridine alkaloids featuring different ring connectivity patterns. The formation of tricyclic benzonaphthyridine rings was identified in the oxidative process. By combining with an intramolecular acylation and the chemoselective late-stage functionalization of pyridine rings, different approaches with 4-10 steps have been designed to accomplish the synthesis of alkaloids demethyldeoxyamphimedine (1), amphimedine (2), meridine (3), isocystodamine (4), N-methylisocystodamine (5), N-hydroxymethylisocystodamine (6), 9-hydroxyisoacididemin (7), neolabuanine A (8), and ecionine A (9).

Synthesis of meridine, cystodamine, and related compounds including iminoquinolinequinone structure

Two aromatic alkaloids, meridine (1) and cystodamine (3), and related compounds (2, 4, 5) were synthesized by hetero Diels-Alder reaction between 4-methoxy- (or 4-chloro-)5,8-quinolinedione and 2-nitrocinnamaldehyde dimethylhydrazone.

Total synthesis of the marine pentacyclic alkaloid meridine

The synthesis of the marine pyridoacridine alkaloid meridine (1) has been accomplished in eight steps from 2,5- 2,5-dimethoxy-3-nitroaniline in 9% overall yield.

Synthesis of meridine, a pentacyclic aza-aromatic alkaloid

A pentacyclic aza-aromatic alkaloid, meridine (1), was synthesized from 4- methoxy-5,8-quinolinedione (4) and o-nitrocinnamaldehyde N,N- dimethylhydrazone (5) in four steps.