111573-52-5

Basic information

• Product Name: 5H-Pyrrolo[1,2-c]imidazol-5-one(9CI)
• Synonyms: 5H-Pyrrolo[1,2-c]imidazol-5-one(9CI);5H-pyrrolo[1,2-c]iMidazol-5-one
• CAS NO: 111573-52-5
• Molecular Formula: C6H4N2O
• Molecular Weight: 120.11
• Product Categories: AMINETERTIARY
• Mol File: 111573-52-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5H-Pyrrolo[1,2-c]imidazol-5-one(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 5H-Pyrrolo[1,2-c]imidazol-5-one(9CI)(111573-52-5)
• EPA Substance Registry System: 5H-Pyrrolo[1,2-c]imidazol-5-one(9CI)(111573-52-5)

Safety Data

• Hazardous Substances Data: 111573-52-5(Hazardous Substances Data)

Usage

Main properties

1. Molecular formula: C5H5N3O
2. Heterocyclic compound
3. Cyclic imide derivative
4. Also known as imidazo[1,2-c]pyrrolo[1,2-a]pyridine-7,9-dione
5. Potential applications in medicinal chemistry
6. Interesting biological activities
7. Important building block for synthesis of various organic compounds
8. Potential uses in material science

Specific content

1. Molecular formula: C5H5N3O
2. Heterocyclic compound: Contains a ring structure with at least two different elements, in this case nitrogen and oxygen atoms.
3. Cyclic imide derivative: Contains an imide functional group, which is a specific type of organic compound containing a nitrogen atom bound to a carbon atom in a carbonyl group.
4. Potential applications in medicinal chemistry: Can be used in the development of pharmaceutical drugs due to its unique biological activities.
5. Interesting biological activities: Possesses properties that make it a promising target for drug discovery and development, indicating potential therapeutic benefits.
6. Important building block for synthesis of various organic compounds: Can be used as a key component in the creation of complex organic molecules in the pharmaceutical and agrochemical industries.
7. Potential uses in material science: Can be utilized in developing new materials and functional molecules, suggesting potential advancements in material technology.

Upstream product

• 91164-68-0 methyl (E)-3-(2H-imidazol-1-yl)-acrylate 
• 3465-72-3 (E)-3-(1H-imidazol-4-yl)propenoic acid 
• 70346-51-9 methyl (E)-3-(1H-imidazol-5-yl)prop-2-enoate 
• 111573-54-7 5--2,2-dimethyl-1,3-dioxane-4,6-dione 

Relevant articles and documents

A stereospecific route to (Z)-Urocanic acids

(Z)-Urocanic acid and its derivatives can be made stereo-specifically by ring-opening of pyrrolo[l,2-c]imidazol-5-ones in aqueous tetrahydrofuran.

A thermal cascade route to pyrroloisoindolone and pyrroloimidazolones

(Chemical Equation Presented) Flash vacuum pyrolysis (FVP) of indol-1-ylacrylate derivatives 11 and 15 or the isomeric indol-3-ylacrylates 21, 22, and 24 at 925°C (0.05 Torr) provides pyrrolo[1,2-a]indol-3-ones 2, 18, 28, and 29 in 53-90% yield by a cascade mechanism that involves a sigmatropic migration, elimination, electrocyclization sequence. Pyrrolo[1,2-a]imidazol-5- ones 3 and pyrrolo[1,2-c]imidazol-5-ones 4 were similarly obtained by FVP of corresponding 2,5-unsubstituted imidazol-1-ylacrylates (e.g., 33), with the former isomer predominating in ca. 80:20 ratio. Migration to the 2-position is therefore favored in the initial sigmatropic shift. FVP of 2-substituted imidazol-1-ylacrylates 35, 37, and 51 (825-875°C) instead give pyrrolo[1,2-c]imidazol-5-ones 56-58 only (88-91%), and that of 4,5-disubstituted imidazol-1-ylacrylates 39 and 41 (825-850°C) provide pyrrolo[1,2-a] imidazol-5-ones 59 and 60 exclusively (93-95%), and thus the selectivity of the initial shift can be controlled by the presence of substituents on the imidazole 2- and 5-positions. FVP of the benzimidazole analogues 61 and 62 at 950°C gave the pyrrolo[1,2-a]benzimidazol-1-ones 6 (71%) and 63 (36%), respectively.

New synthetic routes to pyrrolo-[1,2-a]- and -[1,2-c]-imidazol-5-ones by flash vacuum pyrolysis

1-Substituted and 1,3-disubstituted pyrrolo[1,2-c]imidazol-5-ones 25-27 have been made in fair to excellent yield by flash vacuum pyrolysis (FVP) of the Meldrum's acid precursors 11-13. FVP of the appropriate propenoate precursor 23, 22 and 18-20 gives pyrrolo[1,2-c]imidazol-5-one 2, pyrrolo[1,2-a]-imidazol-5-one 3 and their 6-methyl derivatives 28-30 respectively in 32-90% yield. The mechanism of the propenoate pyrolyses involves rate determining E to Z isomerisation of the alkene followed by elimination of an alcohol and electrocyclisation to the fused ring products.

Synthesis of Pyrroloimidazol-5-one, Pyrroloimidazol-5-one and Pyrrolopyrazol-6-one (Three Isomeric Azapyrrolizinones), by Pyrolysis of Meldrum's Acid Derivatives

Reaction of Meldrum's acid with the imidazole- and pyrazole-carbaldehydes (9)-(11) gave the condensation products (6), (7a), and (8) which were pyrolysed in the gas phase to give the title azaanalogues (2)-(4) of pyrrolizin-3-one (1), as air-sensitive yellow solids.