37842-62-9Relevant academic research and scientific papers
Studies on the π-π Stacking features of imidazole units present in a series of 5-amino-1-alkylimidazole-4-carboxamides
Ray, Sibdas,Das, Aniruddha
, p. 146 - 152 (2015)
Reaction of 2-ethoxymethyleneamino-2-cyanoacetamide with primary alkyl amines in acetonitrile solvent affords 1-substituted-5-aminoimidazole-4-carboxamides. Single crystal X-ray diffraction studies of these imidazole compounds show that there are both anti-parallel and syn-parallel π-π stackings between two imidazole units in parallel-displaced (PD) conformations and the distance between two π-π stacked imidazole units depends mainly on the anti/ syn-parallel nature and to some extent on the alkyl group attached to N-1 of imidazole; molecules with anti-parallel PD-stacking arrangements of the imidazole units have got vertical π-π stacking distance short enough to impart stabilization whereas the imidazole unit having syn-parallel stacking arrangement have got much larger π-π stacking distances. DFT studies on a pair of anti-parallel imidazole units of such an AICA lead to curves for 'π-π stacking stabilization energy vs. π-π stacking distance' which have got similarity with the 'Morse potential energy diagram for a diatomic molecule' and this affords to find out a minimum π-π stacking distance corresponding to the maximum stacking stabilization energy between the pair of imidazole units. On the other hand, a DFT calculation based curve for 'π-π stacking stabilization energy vs. π-π stacking distance' of a pair of syn-parallel imidazole units is shown to have an exponential nature.
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
Das, Aniruddha
, p. 520 - 540 (2017/07/07)
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.
Dimroth-type rearrangement of 1-benzyl- and 1-glycosyl-5-aminoimidazoles to 4-(N-substituted amino)imidazoles
Costanzi, Stefano,Rouse, Sean P.N.,Vanbaelinghem, Laurence,Prior, Timothy J.,Ewing, David F.,Boa, Andrew N.,MacKenzie, Grahame
scheme or table, p. 412 - 415 (2012/02/06)
An efficient route is described to an unusual exocyclic 4-β-d-ribofuranosyl-aminoimidazole nucleoside, related 4-N- benzylaminoimidazoles and imidazole analogues of precursors in the de novo biosynthesis of purines, via a regiospecific and stereoselective
Hydrazine-hydroquinone complex as an efficient solid phase hydrazine donor: High yield synthesis of luminol and isoluminol
Chattopadhyay, Gautam,Ray, Partha Sinha
experimental part, p. 326 - 328 (2011/10/02)
Isomeric aminophthalhydrazides, luminol and isoluminol were easily obtained from the corresponding aminoph-thalimides by solid phase hydrazinolysis with the hydrazine-hydroquinone complex in high yields. Synthesis of a novel chemiluminescent agent, a heterocyclic analogue of isoluminol related to aminoimidazolecarboxamide, is also described.
New purine derivatives of potential plant-growth regulating properties
El-Bayouki,Basyouni,Tohamy
, p. 803 - 820 (2013/05/22)
2-(CHLOROMETHYL)-purine-6(9H)-one (3) was synthesized from reaction of the 5-amino-imidazole-4-carboxamide 1 with 2-chloroacetyl chloride. Also, products 4-7 were obtained from reacting 3 with different reagents. Treatment of 1 with ethyl chloroformate/DMF reagent mixture afforded 9-aryl-1,9-dihydro-6H-purin-6- one (9). Product 9 when reacted with some alkyl iodides gave 7-alkylpurinium iodide salts (10) rather than the expected products of type 11 or 12. N-substituted - purin-6-amines 14a-g, N1-(purin-6-yl) - benzene-1,2-diamine 14h and hydrazide 14i were synthesized upon treating product 9 with phosphoryl chloride followed by reaction with some selected amines or hydrazides. Screening for selected examples from the synthesized products 14 towards wheat plant growth regulation was reported.
Purines, Pyrimidines and Imidazoles. Part 67. Some N-Substituted o-(2-Hydroxyethyl)benzyl-purines, -pyrimidines and -imidazoles as Aromatic Acylonucleoside Analogues
Agathocleous, Demetrios C.,Shaw, Gordon
, p. 2555 - 2560 (2007/10/02)
Reaction of isochromane with hydrogen bromide in acetic acid and further reaction of the products formed with potassium phthalimide gave a mixture of N-phthalimide and N-phthalimide.The mixture, on reactio
Synthesis of Compounds Related to 4(5)-Aminoimidazole-5(4)-carboxamides: Part IV - Synthesis of 2-Substituted 5-Aminothiazoles and Reaction of Related Thiazolium and Imidazolium Salts with Bases
Sen, A. K.,Mukhopadhyay, Ajoy Kumar
, p. 275 - 278 (2007/10/02)
N-Cyanomethylimidates (Ia-e) have been reacted with H2S in pyridine.While ethyl N-(ethoxycarbonylcyanomethyl)acetimidate (Ia), ethyl N-(carbamoylcyanomethyl)acetimidate (Ib) and ethyl N-(carbamoylcyanomethyl)benzimidate (Ic) furnish varying amounts of a mixture of ethyl 5-amino-2-methylthiazole-4-carboxylate (IIIa) and ethyl 2-methyl-4(5)-mercaptoimidazole-5(4)-carboxylate (IVa) (in 2:1 ratio), 5-amino-2-methylthiazole-4-carboxamide (IIIb) and 2-methyl-4(5)-mercaptoimidazole-5(4)-carboxamide (IVb) (in 1:1 ratio) and 5-amino-2-phenylthiazole-4-carboxamide (IIIc) and4(5)-mercapto-2-phenylimidazole-5(4)-carboxamide (IVc) (in 1:5 ratio) respectively, the corresponding formimidates (Id,e) furnish the corresponding thiazole derivatives, ethyl 5-aminothiazole-4-carboxylate (IIId) and 5-aminothiazole-4-carboxamide (IIIe) as the sole products.Reaction of ethyl oximinocyanoacetate (VI) with H2S in pyridine in the presence of ethyl orthoformate, however, produces only the imidazole derivative, ethyl 4(5)-mercaptoimidazole-5(4)-carboxylate (IVd).The changing pattern of the products is interpreted in terms of the formation of thiol and thioamide intermediates.Treatment of 5-amino-1-benzyl-4-carboxamido-2,3-dimethylimidazolium toluene-p-sulphonate and 5-amino-4-carboxamido-1,2,3-trimethylimidazolium toluene-p-sulphonate with aq.NaOH or NaOEt in EtOH effects dequaternization to regenerate 5-amino-1-benzyl-2-methylimidazole-4-carboxamide and 1,2-dimethyl analogue respectively, while the 5-amino-4-ethoxycarbonyl-2,3-dimethylthiazolium toluene-p-sulphonate decomposes on warming with NaOEt in EtOH.
