Synthesis of New bis 1-Substituted 1H-Tetrazoles via Efficient Heterocyclizations from Symmetric Dianilines, Methyl Orthoester, and Sodium Azide

Flores-Reyes, Julio C.; Blanco-Carapia, Roberto E.; López‐Olvera, Alfredo; Islas-Jácome, Perla; Medina-Martínez, Yizrell; Rincón-Guevara, Mónica A.; Ibarra, Ilich A.; Lomas‐Romero, Leticia; González‐Zamora, Eduardo; Islas‐Jácome, Alejandro

doi:10.3390/ecsoc-23-06521

Cited by 3 publications

(2 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthesis of three novel bis-1-substituted-1 H -tetrazoles were reported by Islas-Jácome and co-workers 104 via repetitive-type pseudo-MCR heterocyclizations from symmetric dianilines 666a–c with two equivalents of trimethyl orthoformate ( 664 ), and sodium azide ( 669 ), respectively, in acetic acid as solvent. The proposed mechanism is illustrated in Scheme 68.…”

Section: Repetitive Pseudo-mcrsmentioning

confidence: 99%

Pseudo-multicomponent reactions

et al. 2023

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Repetitive Pseudo-mcrsmentioning

confidence: 99%

Pseudo-multicomponent reactions

et al. 2023

Self Cite

View full text Add to dashboard Cite

show abstract

“…It has a wide use in medicinal chemistry as anti-hyperglycemic [4], antiinflammatory [5][6], antiviral [7][8], anticancer [9], antioxidants [10]. In this study, tetrazole was produced from cyclization of primary amine, sodium azide and triethyl orthoformate [11][12]. Then, the reaction of tetrazole derivative with ethyl cyanoacetate, ammonium acetate and aromatic aldehydes via multicomponent reaction (MCR) for synthesis of pyridine derivatives [13][14] as in the scheme The growth and development of organic synthesis and medicinal chemistry both depend significantly on multicomponent reactions [15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and Theoretical study of some 2-Oxopyridine Carbonitrile derivatives that contain tetrazole ring and evaluation of their Biological activity

Mekky,

Jaber Dalal,

G. Sager

et al. 2023

UTJsci

View full text Add to dashboard Cite

A series of 2-oxo-6-[4-(1H-tetrazol-1-yl) phenyl-1,2-dihydropyridine-3-carbonitrile 3,4-dimethoxyphenyl)-2-oxo-6-4-(1H-tetrazol-1-yl) phenyl]-1,2-dihydropyridine-3-carbonitrile and 2-oxo-6-[4-(1H-tetrazol-1-yl) phenyl]-4-(thiophen-2-yl)- 1,2-dihydropyridine-3-carbonitrile), were prepared from the reaction of 4-aminoacetophenone, sodium azide in the presence of glacial acetic acid via cyclization reaction to produce (1-(4-(1H- 1,2,3,4tetrazole-1-yl) phenyl) ethan-1-one). Followed by condensation of (1-(4-(1H- 1,2,3,4tetrazole-1-yl) phenyl) ethan-1-one) with ethyl cyanoacetate, aromatic aldehydes, and ammonium acetate at 110℃ to give(3,4-dimethoxyphenyl)-2-oxo-6-4-(1H-tetrazol-1-yl)phenyl]-1,2-dihydropyridine-3-carbonitrile and 2-oxo-6-[4-(1H-tetrazol-1-yl) phenyl-1,2-dihydropyridine-3-carbonitrile 3,4-dimethoxyphenyl)-2-oxo-6-4-(1H-tetrazol-1-yl) phenyl]-1,2-dihydropyridine-3-carbonitrile and 2-oxo-6-[4-(1H-tetrazol-1-yl) phenyl]-4-(thiophen-2-yl)- 1,2-dihydropyridine-3-carbonitrile. The synthesized compounds were characterized by spectral methods (FT-IR and 1H-NMR & 13C-NMR). The synthesized compounds have been estimated in lab. for biological efficiency. Preliminary biological testing reveals that the compounds have exhibited activity against the two types of bacteria (staphylococcus aureus, and Klebsiella pneumonia). Both Compounds had high activities. Docking experiments for the compounds were undertaken in order to better understand the ligand-protein interactions in terms were done using py-px and BIOVIA/ Discovery studio of binding affinity. The computed binding affinities were consistent with the MIC values

show abstract

Green Methodologies for Tetrazole Synthesis from Different Starting Materials: A Recent Update

Jaiswal,

Dwivedi,

Kishore

et al. 2024

COC

View full text Add to dashboard Cite

Tetrazole is a most versatile pharmacophore of which more than twenty FDA-approved drugs have been marketed globally for the management of various diseases. In spite of many remarkable and consistent efforts having been made by the chemists towards the development of greener and sustainable strategies for the synthesis of tetrazole derivatives, this approach still needs more attention. The present review focuses on the green synthetic approach for the preparation of tetrazole derivatives from different starting materials such as nitrile, isonitrile, carbonyl, amine, amide, oxime and terminal alkyne functions. The mechanism of tetrazole synthesis from different substrates is discussed. In addition to this, a four component Ugi-azide reaction to the tetrazole synthesis is also described. Of note, the present articles exploited several water-mediated and solventfree methodologies for tetrazole synthesis. The important key features of tetrazole synthesis were pinpointing in each synthetic scheme which provides excellent guide to those searching for selective procedure to achieve the desired transformation. This review seeks to present a timely account (2011-2023) on the splendid array of ecofriendly procedures of synthesis known today for the preparation of tetrazole derivatives from different starting materials. The rational of this review is to enlighten recent advancements in the synthesis of tetrazole derivatives from different substrates.

show abstract

Synthesis of New bis 1-Substituted 1H-Tetrazoles via Efficient Heterocyclizations from Symmetric Dianilines, Methyl Orthoester, and Sodium Azide

Cited by 3 publications

References 28 publications

Pseudo-multicomponent reactions

Pseudo-multicomponent reactions

Synthesis, characterization and Theoretical study of some 2-Oxopyridine Carbonitrile derivatives that contain tetrazole ring and evaluation of their Biological activity

Green Methodologies for Tetrazole Synthesis from Different Starting Materials: A Recent Update

Contact Info

Product

Resources

About