The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles

Goryaeva, M. V.; Burgart, Yanina V.; Ежикова, М. А.; Кодесс, М. И.; Салоутин, В. И.

doi:10.3762/bjoc.11.44

Cited by 18 publications

(10 citation statements)

References 35 publications

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“…Quite interesting heterocyclizations of 5-aminotetrazole were reported by Goryaeva et al ( 2015 ): heterocyclization of 5-aminotetrazole ( 5b ) and 2-ethoxymethylidene-3-oxo esters 240 , depending on the ester type and/or the condition, could give 2-azidopyrimidines 241 or tetrazolo[1,5- a ]pyrimidines 242 . The starting materials under refluxing in EtOH or 1,4-dioxane didn't react completely even after long duration of the treatment and resulted in the formation of inseparable mixtures.…”

Section: Main Partmentioning

confidence: 93%

Aminoazole-Based Diversity-Oriented Synthesis of Heterocycles

et al. 2018

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Section: Main Partmentioning

confidence: 93%

Aminoazole-Based Diversity-Oriented Synthesis of Heterocycles

et al. 2018

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“…Besides increased stability and possibility for preparation of the simplest representatives, improved regioselectivity and increased yields of the condensation products were observed with these building blocks. 17,[40][41][42][43] To the best of our knowledge, synthetic utility of alkoxyvinyl glyoxylates for the construction of fused pyridines was not demonstrated to date. In continuation of our work in the field of pyridine chemistry, [44][45][46][47][48][49][50] we have now aimed at the study of the low-molecular-weight alkoxyvinyl glyoxylates 11a-c as CCC bis-electrophiles in the reactions with common NCC binucleophiles 9 (Scheme 1).…”

Section: Syn Thesismentioning

confidence: 99%

Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

et al. 2020

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An efficient approach to the preparation of pyridine carboxylates fused with 5- or 6-membered heteroaromatic rings is described. The method relied on the Combes-type condensation of the low-molecular-weight β-alkoxyvinyl glyoxylates as CCC bis-electrophiles and with heteroaromatic amines as NCC binucleophiles. In most experiments, β-alkoxyvinyl glyoxylates without additional substituent at the β position led to the corresponding α-pyridine carboxylates (67–87% yield). In the case of β-methyl-substituted derivative, γ-pyridine carboxylates were obtained in 84–99% yield. It was found that regioselectivity of the condensation could be efficiently tuned by changing conditions, such as solvents and acidic additives (HOAc, DMSO or HCl–1,4-dioxane).

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“…2 In view of the above-mentioned facts, if two active pharmacophores, linked together, would generate novel molecular structures which are likely to exhibit interesting biological properties. Tetrazolo-pyrimidine condensed derivatives as the pharmacophore exhibit broad spectrum of biological activities encompassing antimicrobial, [3][4][5][6][7][8] antifungal, [9][10][11] anticancer, [12][13][14][15][16][17][18] antimalarial, 19 antitubercular, 19 anti-inflammatory, 20 analgesics, [21][22] antiviral, 23 anti-oxidant, 24 antiproliferative, [25][26] and antibacterial agents. 27 Hence the preparation of tetrazolo[1,5-a]pyrimidine core unit has gained much importance.…”

Section: Introductionmentioning

confidence: 99%

“…Various methods for the preparation of tetrazolo[1,5-a]pyrimidine derivatives have been cited in literature. [28][29][30][31][32][33][34][35][36][37][38][39][40] However, many of these methods suffered from toxic reagents, harsh reaction conditions, strongly acidic or basic conditions, poor yields, and prolonged reaction-times. We have developed a catalyst free method for the synthesis of 5-(substituted-phenyl)-7-(1H-imidazol-4-yl)-4,7-dihydrotetrazolo-[1,5-a]pyrimidines (5a-n).…”

Section: Introductionmentioning

confidence: 99%

A Facile, Efficient and Catalyst Free Synthesis of Imidazole, Tetrazole and Pyrimidine Combined Moiety as Potential Antimicrobial and Antitubercular Agents

Joshi¹,

Panchani²

2021

HETEROCYCLES

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The tetrazole fused pyrimidine system possesses a broad spectrum of biological activities. So, we have synthesized 5-(substitutedphenyl)-7-(1Himidazol-4-yl)-4,7-dihydrotetrazolo [1,5-a]pyrimidine derivatives (5a-n) by reaction of chalcones with 5-aminotetrazole without catalyst in appropriate solvent. The structural elucidation of these compounds is based on MS, IR, 1 H-NMR and 13 C-NMR spectral data. The in vitro anti-microbial activity was investigated against Gram-positive and Gram-negative bacterial and fungal strains.It was found that the compounds 5a, 5b, 5c, 5d, 5e showed significant activities against tested organisms as compared to standard drugs (Ampicillin and Griseofulvin) while compounds 5a, 5c, 5i, and 5k showed good percentage of average inhibition in the dormant and active stage of tuberculosis.We carried out the synthesis of tetrazolo [1,5-a]pyrimidines in the acidic and basic catalytic amount at reflux temperature, but there was not much satisfied with the yield and reaction time of obtained products.Again the same reaction was carried out without any solvent or catalyst in fused condition but yield was very low. So from the above conclusion, we have chosen, an alcoholic solvents such as methanol, n-propanol, isopropanol, n-butanol and polar solvent like dimethylformamide (DMF) and 1,4-dioxane.After doing various optimizations in the experimental conditions, it was concluded that, when the reaction was carried out in n-butanol solvent showed better yield (87%) in less reaction time.All the newly synthesized compounds were characterized using IR, 1 H-NMR, 13 C-NMR, and mass spectroscopy. The IR spectrum of synthesized compounds exhibited characteristic absorption band at 3075 cm -1 for aromatic C=C stretching vibration band. Characteristic absorption band observed at 1315 cm -1 for C-N stretching in imidazole ring and at 1605 for C=N of the pyrimidine ring system and all other general frequency band are in good agreement with the structure. 1 H-NMR spectra of the compound 5b showed characteristic singlet signals at 12.16 ppm due to the proton of imidazole-NH and at 10.44 ppm due to the proton of fused pyrimidine-NH. Chiral carbon proton was observed doublet at 5.28 ppm with 2.80 Hz coupling constant value. The 1 H-NMR spectrum of compound 5c exhibited two doublets, arising from the two equivalent phenyl ring protons at 7.54 and 7.24 ppm. The 13 C-NMR spectrum of compound 5c showed signal at 53.23 ppm for the chiral carbon while at 96.00 ppm for the pyrimidine ring C=C carbon and at 21.12 ppm for the methyl carbon attached to phenyl ring. Molecular ion peak was observed in agreement with molecular weight of respective compound i.e. the molecular formula of compounds 5c and 5m by displaying molecular ion peaks at m/z 279 (M + ) and 325 (M + ) respectively. Scheme 1 PLAUSIBLE REACTION MECHANISM: Scheme 2The examination of the data of the Table 2 revealed that many of the compounds shown good activity against bacterial strain when compared with the standard drugs like Ampicillin, Chloramphenicol, and...

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The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles

Cited by 18 publications

References 35 publications

Aminoazole-Based Diversity-Oriented Synthesis of Heterocycles

Aminoazole-Based Diversity-Oriented Synthesis of Heterocycles

Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

A Facile, Efficient and Catalyst Free Synthesis of Imidazole, Tetrazole and Pyrimidine Combined Moiety as Potential Antimicrobial and Antitubercular Agents

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