Tandem in situ generation and 1,5-electrocyclization of N-hetaryl nitrilimines. A facile methodology for synthesis of annulated 1,2,4-triazoles and their acyclo C-nucleosides

Shawali, Ahmad S.

doi:10.3998/ark.5550190.0011.102

Cited by 4 publications

(1 citation statement)

References 56 publications

(62 reference statements)

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“…[ 6a ] Huisgen is also a trailblazer in 1,3‐dipolar cycloaddition, which is efficient for constructing five‐membered rings. [ 6b ] A major application of 1,5‐electrocyclization is the efficient construction of five‐membered heterocycles [ 7 ] which can be applied to total synthesis. At the same time, 1,5‐electrocyclization has been widely used in the field of photochromism.…”

Section: Introductionmentioning

confidence: 99%

Overview of 6π 1,5‐Electrocyclization over the Past 40 Years

2023

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Comprehensive Summary As an important part of pericyclic reaction, 6π 1,5‐electrocyclization plays an important role in organic synthesis and chemical theory. Many types of five‐membered rings could be constructed via 1,5‐electrocyclization with high atom economy. Some elegant works have been reported in this field in the past few decades. However, it still needs a lot of effort in further advancements of 1,5‐electrocyclization. This review summarized the development of 1,5‐electrocyclization relying on stepwise, stoichiometric, or catalytic approaches. The 1,5‐electrocyclization reaction will be divided into three categories: aza 1,5‐electrocyclization, all‐carbon 1,5‐electrocyclization and other heteroatoms (O, P, S) involved 1,5‐electrocyclization, and related mechanistic studies will also be involved in this review.

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Section: Introductionmentioning

confidence: 99%

Overview of 6π 1,5‐Electrocyclization over the Past 40 Years

2023

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ChemInform Abstract: Tandem in situ Generation and 1,5‐Electrocyclization of N‐Hetaryl Nitrilimines: A Facile Methodology for the Synthesis of Annulated 1,2,4‐Triazoles and Their Acyclo C‐Nucleoside

Shawali

2010

ChemInform

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Synthesis, reactions, and antimicrobial activity of some novel pyrazolo[3,4‐d]pyrimidine, pyrazolo[4,3‐e][1,2,4]triazolo[1,5‐c]pyrimidine, and pyrazolo[4,3‐e][1,2,4]triazolo[3,4‐c]pyrimidine derivatives

Hassaneen

Saleh

Abdallah

et al. 2019

Journal of Heterocyclic Chem

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Treatment of N-phenyl-substituted benzenecarbo-hydrazonoyl chlorides 1ad with malononitrile in sodium ethoxide solution gave 5-amino-4-cyanopyrazole derivatives 2-5. Compounds 2-5 were converted to formidate derivatives 6-9 upon treatment with TEOF in acetic anhydride. The reaction of the latter products 6-9 with hydrazine hydrate gave imino-amino derivatives 10-13, which was converted to hydrazino derivatives 14-17 by refluxing with hydrazine hydrate. Hydrazino as well as imino-amino derivatives undergo condensation, cyclization, and cycloaddition reactions to give pyrazolo[3,4-d]pyrimidine 18-21, pyrazolo[4,3-e][1,2,4]triazolo-[3,4-c]pyrimidine 22-27, and pyrazolo[3 0 ,4 0 :4,5]pyrimido[1,6-b][1,2,4]triazine 42-44 derivatives. Antimicrobial studies are performed using two Gram-positive bacteria and two Gram-negative bacteria. Data indicated that compounds 5, 28D, 29B, and 31D are exploring elevated antibacterial effects against all strains tested. Compound 28D is the most promising antibacterial agent against the delicate bacterial strain Bacillus subtilis and Pseudomonas aeruginosa with high effectiveness (low minimum inhibitory concentration [MIC] value) 40 and 60 μg/mL, respectively.

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Tandem in situ generation and 1,5-electrocyclization of N-hetaryl nitrilimines. A facile methodology for synthesis of annulated 1,2,4-triazoles and their acyclo C-nucleosides

Cited by 4 publications

References 56 publications

Overview of 6π 1,5‐Electrocyclization over the Past 40 Years

Overview of 6π 1,5‐Electrocyclization over the Past 40 Years

ChemInform Abstract: Tandem in situ Generation and 1,5‐Electrocyclization of N‐Hetaryl Nitrilimines: A Facile Methodology for the Synthesis of Annulated 1,2,4‐Triazoles and Their Acyclo C‐Nucleoside

Synthesis, reactions, and antimicrobial activity of some novel pyrazolo[3,4‐d]pyrimidine, pyrazolo[4,3‐e][1,2,4]triazolo[1,5‐c]pyrimidine, and pyrazolo[4,3‐e][1,2,4]triazolo[3,4‐c]pyrimidine derivatives

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