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General Description

1H-Imidazole-4-carboxamide, 5-amino-1-phenyl- is a chemical compound with the molecular formula C9H9N3O. It belongs to the imidazole class of compounds and is a derivative of 1H-imidazole-4-carboxamide. It is characterized by its aromatic phenyl group and amino group attached to the imidazole ring. 1H-Imidazole-4-carboxamide, 5-amino-1-phenyl- has several potential biological activities and has been studied for its potential use as a pharmaceutical drug. It may have applications in the treatment of various diseases and conditions, and further research is ongoing to explore its potential uses.

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 62-53-3 aniline 
• 6719-21-7 2-Amino-2-cyanoacetamide 
• 3849-20-5 2-cyano-2-oximinoacetamide 
• 37842-62-9 ethyl N-(carbamoylcyanomethyl)formamidate 

Downstream Products

• 6334-42-5 1,9-dihydro-9-phenyl-6H-purin-6-one 
• 5444-47-3 9-phenyl-3,9-dihydro-purine-2,6-dione 
• 155579-42-3 5-amino-1-phenyl-1H-imidazole-4-carbonitrile 
• 5470-24-6 6-Chloro-9-phenyl-9H-purine 
• 220876-79-9 1-phenyl-5-chloroacetamidoimidazole-4-carboxamide 

Relevant academic research and scientific papers

Studies on complex π-π and T-stacking features of imidazole and phenyl/p-halophenyl units in series of 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carboxamides and their carbonitrile derivatives: Role of halogens in tuning of conformation

5-amino-1-(phenyl/p-halophenyl)imidazole-4-carboxamides (N-phenyl AICA) (2a-e) and 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carbonitriles (N-phenyl AICN) (3a-e) had been synthesized. X-ray crystallographic studies of 2a-e and 3a-e had been performed to identify any distinct change in stacking patterns in their crystal lattice. Single crystal X-ray diffraction studies of 2a-e revealed π-π stack formations with both imidazole and phenyl/p-halophenyl units in anti and syn parallel-displaced (PD)-type dispositions. No π-π stacking of imidazole occurred when the halogen substituent is bromo or iodo; π-π stacking in these cases occurred involving phenyl rings only. The presence of an additional T-stacking had been observed in crystal lattices of 3a-e. Vertical π-π stacking distances in anti-parallel PD-type arrangements as well as T-stacking distances had shown stacking distances short enough to impart stabilization whereas syn-parallel stacking arrangements had got much larger π-π stacking distances to belie any syn-parallel stacking stabilization. DFT studies had been pursued for quantifying the π-π stacking and T-stacking stabilization. The plotted curves for anti-parallel and T-stacked moieties had similarities to the ‘Morse potential energy curve for diatomic molecule’. The minima of the curves corresponded to the most stable stacking distances and related energy values indicated stacking stabilization. Similar DFT studies on syn-parallel systems of 2b corresponded to no π-π stacking stabilization at all. Halogen-halogen interactions had also been observed to stabilize the compounds 2d, 2e and 3d. Nano-structural behaviour of the series of compounds 2a-e and 3a-e were thoroughly investigated.

A domino type one-flask synthesis of 1-substituted-5-aminoimidazole-4- carboxamides and ring transformation to pyrazine under microwave through suitable aminoimidazoliumcarboxamide

Reductive heterocyclisation of oximinocyanoacetamide 1 in the presence of ethyl orthoformate and appropriate amine affords 1-substituted-5-aminoimidazole- 4-carboxamides 2. 4-Amino-5-carboxamido-3-diphenylmethyl-1-phenacylimidazolium bromide 4c, generated

Synthesis of crown containing imidazo[4,5-e] and -[5,4-e][1,4]diazepines

Starting from benzocrown substituted 4(5)-aminoimidazole-5(4)-carboxamides we have, for the first time, prepared benzocrown imidazo[4,5-e]- and -[5,4-e][1,4]diazepines - cyclic homologs of the corresponding xanthines. 1998 Plenum Publishing Corporation.