2 edition of chemistry of imidazo [5, 1-c] [1, 2, 4] triazines. found in the catalog.
chemistry of imidazo [5, 1-c] [1, 2, 4] triazines.
Ghouse Unissa Baig
by University of Aston in Birmingham. Department of Pharmacy in Birmingham
Written in English
Thesis (M.Phil.) - University of Aston in Birmingham 1980.
In , Biotie Therapies and Wyeth claimed a series of 1,2,4-triazine- and pyrazine-containing tricyclic compounds exhibiting dual inhibition against both PDE2A and PDE10A as therapeutic targets [25,26,27,28].The triazine series comprises benzo- and pyridine-fused imidazo[5,1-c][1,2,4]triazine derivatives , some of which are depicted in Figure 1 (Compounds I (TA1), II, and III), along with. Reactions with hydrazonoyl halides Synthesis and antimicrobial evaluation of some new imidazo[1,2‐a ]pyrimidine, imidazo [1,2‐a ]pyridine, imdazo[1,2‐b ]pyrazole, and quinoxaline derivatives.
Sorry, our data provider has not provided any external links therefore we are unable to provide a link to the full text. The chemistry of imidazo [5, 1-c] [1, 2, 4] triazines Author: Baig, G. U. ISNI: Awarding Body: University of Aston in Birmingham Current Institution: Aston University Date of Award: Availability of Full Text: Access from EThOS.
Synthetic methods, reactivity, and the properties of a new class of antiviral compounds, pyrazolo-, imidazo-, 1,2,4-triazolo[5,1-c]-1,2,4-triazinones, tetrazolo[5,1-b]-1,2,4-triazinones, and azoloannulated amino-1,2,4-triazines having structural similarity with biogenic purines and capable of mimicking them in metabolic processes are considered. Synthesis of several new diphenyl-1',2',4'-triazin-3'-yl barbituric acid are described. The method involves addition reaction of isocyanate and isothiocyanate and 3-amino-5,6-diphenyl-1,2,4-triazine (1) to give N1,N3-disubstituted urea 2 and N1,N3-disubstituted thioureas 3 and 4 respectively. Further, ring closure reactions with malonate ester give barbituric acid 5 and thiobarbituric acid 6.
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The 3-β-D-ribofuranoside 6 of the new imidazo[2,1-f][1,2,4]triazine chemistry of imidazo [5 is isomeric and isoelectronic with the nucleoside deaminoformycin 1 which is a good inhibitor of adenosine deaminase (ADA) while its 5′-monophosphate 2 is a good inhibitor of adenosine 5′-monophosphate deaminase (AMPDA).The 6-methylsulfanyl derivative 7 of 6 is synthesized by condensation of the monocyclic 1,2,4 Cited by: 4-(Substituted)imidazo[5,1-c][1,2,4)triazinecarboxamides with ester, ketone, or cyano-groups in the 3-position undergo ring-opening with hydrazine 4] triazines.
book phenylhydrazine to yield substituted (pyrazolylidenehydrazino) some cases ring cleavage is initiated by attack of the hydrazine at C-4 of the imidazotriazine, and in others by nucleophilic attack at the 3.
5-Diazomidazolecarboxamide couples with reactive methylenic substrates to afford a series of imidazolyl-hydrazones which cyclise in acid or alkali to imidazo[5,1-c][1,2,4]ones with cyano-substituents cyclise in acid to yield 7-aminoimidazotriazines whereas hydrazones with acetyl groups undergo acidic dehydration to form bicycles with a 7-methylene substituent.
Synthesis of detomidine and medetomidine metabolites: 1,2,3-trisubstituted arenes with 4′(5′)-imidazolylmethyl groups. Journal of Heterocyclic Chemistry30 (6), Cited by: Imidazo[5,1-f][1,2,4]triazinones, as isosteres of purine, are of interest for pharmaceutical research. The syntheses reported in the literature generally require several steps.
We report a novel method to access a broad range of diversely substituted derivatives. The key step is the electrophilic N-amination of 3H-imidazoles containing a 4-carbonyl by: The synthesis of the potential bronchodilators 2-aminomethylpropylimidazo[5,1-f][1,2,4]triazin-4(3H)-one (12) and fhe corresponding triazine (2) is described and some chemical reactions of this novel ring system are gh X-ray analysis of the methanesulphonate salt of (12) indicated that protonation occurred on the nitrogen atom at position 6, acylation of the primary amino.
Two different fused imidazoles, imidazo[2,1-c][1,2,4]triazines (extensive literature data) and imidazo[5,1-c][1,2,4]triazines (much less information), are discussed in this section.
All synthetic approaches to imidazo[2,1- c ][1,2,4]triazines published during recent years utilize the ring closure of the six-membered triazine ring by conversion. Neunhoeffer, in Comprehensive Heterocyclic Chemistry, 1,2,3,5-Tetrazines.
Of the three possible tetrazine systems the 1,2,3,5-tetrazines (24), also called as-tetrazines, are by far the least studied compound with this structure was mentioned in the last review 〈78HC(33)〉, which covered the literature through Chemical Abstracts Triazine chemistry in general has shown an incredible growth inas already mentioned.
This is more especially true for a-triazines, for which about 40 publications on their synthetic chemistry have appeared, more than during all the years before!However, most reports are related to substituent conversions.
First of all, a minireview appeared focusing on a-triazine-bearing pyrazoline. Imidazo[4,5-d][1,2,3]triazines (1) Previous syntheses of this system have been carried out exclusively by the nitrous acid cyclization of 5-aminoimidazolecarboxamides.
An interesting variation on this theme is seen in Scheme 9 where the O -methylamidoxime () forms the 3- N -oxide (58) (50%) via the salt () 〈90H( A series of triazinic inhibitors of focal adhesion kinase (FAK) have been recently shown to exert antiangiogenic activity against HUVEC cells and anticancer efficacy against several cancer cell lines.
We report herein that we further explored the heterocyclic core of these inhibitors by a fused imidazole ring with the triazine to provide imidazo[1,2-a][1,3,5]triazines. The pyrrolo[2,1-f][1,2,4]triazine nucleus was identified as a novel kinase inhibitor template which effectively mimics the well-known quinazoline kinase inhibitor scaffold.
Attachment of a 4-((3-chlorofluorophenyl)amino) substituent to the template provided potent biochemical inhibitors of the tyrosine kinase activity of EGFR, as well as inhibition of cellular proliferation of the human. A series of novel acylamino α-keto-esters (4) have been prepared via a Dakin–West reaction of acylated a-aminoacids and ethyl oxalyl chloride.
Their use in a general synthesis of imidazo[5,1-f]-1,2,4-triazin-4(3H)-ones (7) is conversion of the imidazotriazinones into the corresponding imidazo[5,1-f]-1,2,4-triazines (20) and their 3,4-dihydro-derivatives (19) are also reported.
The synthesis of several new 4‐mono‐ and 2,4‐disubstituted pyrrolo[2,1‐f ][1,2,4]triazines is described.
Key 1‐aminopyrrole‐2‐carbonitrile intermediates 3 and 15 were obtained by N ‐amination of the corresponding pyrrole‐2‐carboxaldehyde followed by CHO → CN conversion with either hydroxylamine‐O ‐sulfonic acid for 3.
Versatile straightforward synthetic pathways for a novel series of annelated imidazo[2,1-c][1,2,4]triazole derivatives were performed.
• The newly synthesized compounds were synthesized from the reactive binucleophile 3-hydrazinyl(4-methoxybenzylidene)phenyl-5H-imidazo [2,1-c][1,2,4]triazol-6(7H)-one 2 applying different synthetic.
Summary This chapter contains sections titled: Introduction Uncondensed 1,2,4‐Trianzines 1,2,4‐Triazine Rings Condensed with Carbocycles 1,2,4‐Triazine Rings Condensed with Heterocycles The 1,2,4‐Triazines - Erickson - - Chemistry of Heterocyclic Compounds: A Series Of Monographs - Wiley Online Library.
We studied the reactivity of diethyl 4-aminoimidazo[5,1-с][1,2,4]triazine-3,8-dicarboxylate in reactions with nucleophiles and demonstrated the possibility of selective formation of monoamides by interaction with primary and secondary aliphatic amines.
Synthesis and In Vitro Evaluation of 8-Pyridinyl-Substituted Benzo[e]imidazo[2,1-c][1,2,4]triazines as Phosphodiesterase 2A Inhibitors by Rien Ritawidya 1,2,*, Friedrich-Alexander Ludwig 1, Detlef Briel 3, Peter Brust 1 and Matthias Scheunemann 1,*.
Synthesis of new heteroaromatic systems: Naphth[2,1-e]imidazo[5,1-c]-1,2,4-triazines and benzimidazo-[5,1-c]-1,2,4-triazines M. Bezmaternykh, V. Mokrushin Pages J. Org. Chem. All Publications/Website. OR SEARCH CITATIONS. Abstract A convenient synthesis of a series of pyrazole, pyridine, pyridinethione, pyridazine, pyrazolo[3,4-b]pyridine, imidazo[1,2-a]pyrimidine, and pyrazolo[5,1-c][1 2 4]triazine derivatives incorporating a pyrimidine moiety, via the reactions of the versatile, readily accessible 3-oxo-N-(pyrimidyl)butanamide with the appropriate reagents, is described.Synthesis of 6,8-substituted derivatives of imidazo[5,1-c][1,2,4]triazines and 1,4-dihydroimidazo[5,1-c][1,2,4]triazinones M.
A. Bezmaternykh, V. S. Mokrushin, T. A. Pospelova Pages Analogously, (1,2,3‐triazol‐4‐yl)thieno[2,3‐b ]pyridine derivatives were obtained from sodium 3‐hydroxy‐1‐(5‐methyl‐1‐phenyl‐1H‐1,2,3‐ triazole‐4‐yl)prop‐2‐en‐1‐one and cyanothioacetamide followed by its reacting with active methylene compounds.
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