68282-50-8

Usage

Physical form

Yellow crystalline solid

Common uses

Organic synthesis, pharmaceutical research

Role

Key intermediate in the synthesis of various pharmaceutical compounds, building block for the preparation of heterocyclic compounds

Properties

Aromatic, imidazolic, unique structure valuable for drug development and chemical research

Potential applications

Medicine, biotechnology, pharmacological properties

Importance

Crucial in the development of novel drugs and pharmaceuticals

Upstream product

• 108512-07-8 N-(3-methyl-4-isoxazolyl)benzamide 
• 77335-93-4 ethyl 4-methyl-2-phenyl-1H-imidazole-5-carboxylate 
• 13682-32-1 4-Hydroxymethyl-5-methyl-2-phenyl-3H-imidazole 
• 1670-14-0 benzamidine monohydrochloride 
• 98-88-4 benzoyl chloride 

Downstream Products

• 13682-20-7 4,5-dimethyl-2-phenyl-1H-imidazole 
• 13682-32-1 5-Methyl-2-phenyl-4-imidazolemethanol 
• 119514-71-5 2-phenyl-4-(1-hydroxy-2-methylpropyl)-5-methyl-1H-imidazole 
• 10045-55-3 2-phenyl-4-(1-hydroxyethyl)-5-methylimidazole 
• 195606-24-7 5-(2-Phenyl-5-methyl-3H-imidazol-4-ylmethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 69433-89-2 8-methyl-4-methylsulfanyl-6-phenyl-imidazo[1,5-d][1,2,4]triazine 
• 68282-92-8 8-methyl-6-phenyl-3H-imidazo[1,5-d][1,2,4]triazine-4-thione 
• 68283-02-3 8-methyl-6-phenyl-3H-imidazo[1,5-d][1,2,4]triazin-4-one 
• 68283-55-6 3,8-dimethyl-6-phenyl-3H-imidazo[1,5-d][1,2,4]triazine-4-thione 
• 68283-51-2 3,8-dimethyl-6-phenyl-3H-imidazo[1,5-d][1,2,4]triazin-4-one 
• 69784-47-0 4-benzoyloxy-8-methyl-6-phenyl-imidazo[1,5-d][1,2,4]triazine 
• 69784-46-9 4-butyryloxy-8-methyl-6-phenyl-imidazo[1,5-d][1,2,4]triazine 
• 69784-45-8 4-acetoxy-8-methyl-6-phenyl-imidazo[1,5-d][1,2,4]triazine 

Relevant academic research and scientific papers

Synthesis and pharmacological evaluation of a novel series of 3-aryl-2-(2-substituted-4-methylthiazole-5-yl)thiazolidin-4-one as possible anti-inflammatory and antimicrobial agents

A new series of 3-aryl-2-(2-aryl/benzyl-4-methylthiazole-5-yl)thiazolidin- 4-one was synthesized by condensation of 2-aryl/benzyl-4-methylthiazole-5- carbaldehyde, aromatic amines and thioglycolic acid in toluene. All the synthesized compounds are characterized by IR, NMR and elemental or mass analysis. Sixteen out of the newly synthesized compounds were screened for in vivo anti-inflammatory activity using carrageenan-induced rat paw edema method. Some of the synthesized compounds exhibited good anti-inflammatory activity compared with indomethacin. The synthesized compounds were also evaluated for their in vitro antimicrobial activity. Some of the compounds showed mild antibacterial activity while most of the compounds showed good antifungal activity.

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 4(5)-Acyl-, 1-Substituted 5-Acyl, and 1-Substituted 4-Acyl-1H-imidazoles from 4-Aminoisoxazoles

4-Aminoisoxazoles can be acylated with a wide variety of activated carboxylic acids.Hydrogenation of the resulting amides gives α-(acylamino)enaminones, which cyclize to 4(5)-acylimidazoles upon treatment with base.This method allows for the synthesis of acylimidazoles with a wide range of substituents at C-2.Utilization of N-substituted 4-aminoisoxazoles in the same sequence of reactions yields 1-substituted 5-acylimidazoles, a substitution pattern not otherwise easily prepared.Treatment of α-(acylamino)enaminones, derived from N-unsubstituted isoxazoles, with primary amines leads to incorporation of the amine at the β-position with concomitant expulsion of ammonia.This sequence efficiently yields 1-substituted and 1,2-disubstituted 4-acylimidazoles but does not give satisfactory yields of 5-substituted 4-acylimidazoles due to steric inhibition of the amine exchange.

Imidazo[1,5-d]-as-triazine-4(3H)-ones and thiones

There is provided substituted imidazo[1,5-d]-as-triazine-4(3H)-ones and substituted imidazo[1,5-d]-as-triazin-4(3H)-thiones useful as inhibitors of the enzyme cyclic-AMP phosphodiesterase and as broad spectrum herbicides.

Method for the control of undesired plant species using imidazo-as-triazinones and triazine-thiones

This disclosure describes herbicidal methods for the pre- and postemergence control of undesired mono- and dicotyledonous plants using substituted imidazo[1,5-d]-as-triazin-4(3H)-ones and substituted imidazo[1,5-d]-as-triazine-4(3H)-thiones.

SUBSTITUTED 3-(4-IMIDAZOLYLMETHYLENE)CARBAZIC AND THIOCARBAZIC ACID ESTERS

There are provided substituted 3-(4-imidazolyl-methylene)carbazic acid esters and 3-(4-imidazolylmethylene)dithiocarbazic acid esters useful as intermediates for the preparation of compounds which inhibit the enzyme cyclic-AMP phosphodiesterase

IMIDAZO [1,5-d]-AS-TRIAZINE-4(3H)-ONES AND THIONES

There is provided substituted imidazo[1,5-d]-as-triazine-4(3H)-ones and substituted imidazo[1,5-d]-as-triazin-4(3H)-thiones useful as inhibitors of the enzyme cyclic-AMP phosphodiesterase and as broad spectrum herbicides