Synthesis of 6-Amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles Catalyzed by Silica-Supported Tetramethylguanidine Under Solvent-Free Conditions

doi:10.1080/00397911.2014.913634

Paper

Synthesis of 6-Amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles Catalyzed by Silica-Supported Tetramethylguanidine Under Solvent-Free Conditions

Published May 19, 2014 · A. B. Atar, Jong Tae Kim, K. Lim

Synthetic Communications

Q3 SJR score

42

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Abstract An efficient, high-yielding, and rapid protocol has been developed for the synthesis of diversity-oriented 6-amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles derivatives via a four-component, one-pot cyclocondensation reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile using silica-supported tetramethylguanidine as a heterogeneous catalyst for the first time. The protocol proves to be efficient and environmentally benign in terms of very easy workup, good yields, and ease of recovery of catalyst. In addition, the present method is superior in terms of green media, the amount of catalyst, and reaction time. GRAPHICAL ABSTRACT

Study Snapshot

This study developed an efficient, environmentally benign, and rapid method for synthesis of diverse 6-amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles using silica-supported tetramethylguanidine under solvent-free conditions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Synthesis of 6-Amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles Catalyzed by Silica-Supported Tetramethylguanidine Under Solvent-Free Conditions

Sign up to use Study Snapshot

References

Meglumine promoted one-pot, four-component synthesis of pyranopyrazole derivatives

Meglumine is a highly efficient and reusable catalyst for the one-pot, four-component synthesis of pyranopyrazole derivatives at room temperature, with broad substrate scope and no hazardous organic solvents.

Synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles using disulfonic acid imidazolium chloroaluminate as a dual and heterogeneous catalyst

Disulfonic acid imidazolium chloroaluminate [Dsim]AlCl4 is a green, simple, and efficient catalyst for the green, simple, and efficient synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano

Heterogenized tungsten complex: an efficient and high yielding catalyst for the synthesis of structurally diverse tetra substituted pyrrole derivatives via four-component assembly

This study developed an efficient, high-yielding method for synthesis of diverse pyrrole derivatives using silica supported tungstic acid, offering high atom-economy, operational simplicity, shorter reaction time, convergence, and facile automation.

Multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles catalyzed by lipase from Aspergillus niger

Lipase from Aspergillus niger effectively catalyzes the four-component synthesis of dihydropyrano[2,3-c]pyrazoles, offering environmental friendliness, reusability, room temperature conditions, and excellent yields.

A highly efficient, rapid one-pot synthesis of some new heteroaryl pyrano[2,3-c]pyrazoles in ionic liquid under microwave-irradiation

This one-pot method efficiently synthesizes indolyl- and quinolylpyrano[2,3-c]pyrazoles in ionic liquid under microwave irradiation, potentially displaying antitubercular activity.

Citations

Construction of a Dual-Functionalized Acid-Base Nanocatalyst via HEPES Buffer Functionalized on Fe3O4 as a Reusable Catalyst for Annulation Reactions.

Fe3O4@GLYMO-HEPES is a highly efficient, recyclable, and stable nanocatalyst for various applications, including the synthesis of various fused heterocycles.

Medicinal Chemistry & Drug Discovery

Recent studies have shown mild, green, and environmentally friendly methods for synthesizing pyranopyrazole derivatives, improving yields and binding interactions for pharmaceutical and agrochemical industries.

Yolk-shell structured magnetic mesoporous organosilica supported ionic liquid/Cu complex: an efficient nanocatalyst for the green synthesis of pyranopyrazoles

The YS-Fe3O4@PMO/IL-Cu nanocatalyst is a highly recyclable, selective, and effective nanocatalyst for the green synthesis of pyranopyrazoles under ultrasonic media.

l–aspartic acid chelan–Cu (II) complex coted on ZrFe2O4 MNPs catalyzed one–pot annulation and cooperative geminal-vinylogous anomeric–based oxidation reactions

The novel l-aspartic acid chelan-Cu (II) complex on ZrFe2O4 MNPs effectively catalyzes one-pot annulation and cooperative geminal-vinylogous anomeric-based oxidation reactions, offering potential for high-performance catalysis

Synthesis of Pyrazolopyranopyrimidine and Dihydropyrano[2,3-c]Pyrazole Derivatives Using Fe3O4@THAM-Piperazine as a Superparamagnetic Nanocatalyst under Green Condition

This study presents a simple, green, and recyclable method for preparing pyrazolopyranopyrimidine and dihydropyrano[2,3-c]pyrazole derivatives using Fe3O4@THAM-piperazine as a superparamagnetic nanocataly

Recent advances in the synthesis of pyrazole scaffolds via nanoparticles: A review

Nanoparticles have shown promising potential in the synthesis of various pyrazole derivatives, which possess significant biological and pharmacological activities.

Urea chelated autocombused synthesis of BiFeO3 nanoparticles: application as magnetically retriable heterogeneous catalyst for synthesis of pyrano[2,3-c] pyrazoles

BiFeO3 nanoparticles show promising heterogeneous catalytic performance for one-pot production of pyrano[2,3-c] pyrazoles, with optimal results achieved at 650°C.