Pyrrolo[2,1-a]isoquinoline

Base Information

• Chemical Name: Pyrrolo[2,1-a]isoquinoline
• CAS No.: 234-92-4
• Molecular Formula: C12H9 N
• Molecular Weight: 167.21
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30559839
• Nikkaji Number: J3.201.989G
• Wikidata: Q82442698
• Mol file: 234-92-4.mol

Synonyms:pyrrolo(2,1-a)isoquinoline

Chemical Property of Pyrrolo[2,1-a]isoquinoline

Chemical Property:

• Melting Point: 83.5-84 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• PSA: 4.41000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 3.09250
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 167.073499291
• Heavy Atom Count: 13
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

Pyrrolo[2,1-a]isoquinoline 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CN3C2=CC=C3
• General Description: Pyrrolo[2,1-a]isoquinoline, also known as Benz[g]indolizine or Benzopyrrocoline, is a heterocyclic compound with notable biological activities, including anti-depressant, calcium entry blocking, and anticancer properties. It can be synthesized efficiently through methods such as one-pot reactions in aqueous media or asymmetric synthesis using chiral formamidines, yielding high-purity products under mild conditions. These synthetic approaches highlight its potential as a pharmacologically relevant scaffold.

Technology Process of Pyrrolo[2,1-a]isoquinoline

There total 9 articles about Pyrrolo[2,1-a]isoquinoline 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: 88.0%

2-Methylthiopyrrolo<2,1-a>isoquinoline (102053-04-3) → pyrrolo[2,1-a]isoquinoline (234-92-4)

Guidance literature:

With nickel; In ethanol; for 10h; Heating;

Reference yield:

2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline (853925-56-1) → pyrrolo[2,1-a]isoquinoline (234-92-4)

Guidance literature:

With palladium on activated charcoal; naphthalene; carbon dioxide;

DOI:10.1021/ja01111a022

Reference yield:

N-(2-phenylethyl)pyrrolidin-2-one (10135-23-6) → pyrrolo[2,1-a]isoquinoline (234-92-4)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphorus (V)-oxide; tetralin

2: palladium/charcoal; naphthalene; carbon dioxide

With palladium on activated charcoal; naphthalene; tetralin; carbon dioxide; phosphorus pentoxide;

DOI:10.1021/ja01111a022

upstream raw materials:

2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline

2-Methylthiopyrrolo<2,1-a>isoquinoline

2-ethoxycarbonyl-methylisoquinolinium bromide

2-<1-ethoxycarbonyl-2,2-bis(methylthio)ethenyl>isoquinolinium iodide

Refernces

Efficient synthesis of pyrrolo[2,1-a]isoquinoline and pyrrolo[1,2-a] quinoline derivatives in aqueous media

10.1002/jhet.205

The research focuses on the efficient synthesis of pyrrolo[2,1-a]isoquinolines and pyrrolo[1,2-a]quinolines, which are significant due to their potential applications as central nervous system depressants, calcium entry blockers, and anticancer agents, among others. The study aims to develop a more efficient and environmentally friendly method for synthesizing these compounds by conducting the reactions in aqueous media. The researchers successfully reported a one-pot procedure using quinoline or isoquinoline, phenacylbromide derivatives, and activated alkynes, which resulted in good to excellent yields of the desired heterocyclic compounds. The method offers the advantages of simple operation, mild reaction conditions, high product yields, and cost-effectiveness, demonstrating the potential of water as an efficient promoter in chemical transformations.

A CONVENIENT ASYMMETRIC SYNTHESIS OF PYRROLO<2,1-a>ISOQUINOLINES

10.1016/0040-4039(90)80155-F

The research focuses on the asymmetric synthesis of pyrrolo[2,1-a]isoquinolines, a class of compounds with significant anti-depressant activity. The purpose of the study was to develop a convenient and efficient four-step synthesis method for optically pure Ga-phenyl pyrroloisoquinolines starting from chiral formamidines. The process involved metalation with s-BuLi or t-BuLi at -78°C, followed by alkylation with 1-chloro-3-iodopropane at -100°C, and removal of the formamidine auxiliary to produce the secondary amine, which spontaneously cyclized to form the desired compounds. The method was found to be effective, yielding the products in good yield and high optical purity. Key chemicals used in the process included 4-phenyl-1,2,3,4-tetrahydroisoquinoline, dimethylaminoformamidine, P-methyl-1-methoxypropyl amine, and 1-chloro-3-iodopropane, among others.

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