Chalcone-Based Synthesis of Tetrahydropyridazines via Cloke–Wilson-Type Rearrangement-Involved Tandem Reaction between Cyclopropyl Ketones and Hydrazines

Meng, Yingfen; Gu, Jiayi; Xin, Meixiu; Jiang, Yi; Du, Zhibo; Lu, Guoqing; Jiang, Jiayao; Chan, Albert S. C.; Ke, Zhuofeng; Zou, Yong

doi:10.1021/acs.joc.3c02824

J. Org. Chem.

2024

DOI: 10.1021/acs.joc.3c02824

|View full text |Cite

Chalcone-Based Synthesis of Tetrahydropyridazines via Cloke–Wilson-Type Rearrangement-Involved Tandem Reaction between Cyclopropyl Ketones and Hydrazines

Yingfen Meng,

Jiayi Gu,

Meixiu Xin

et al.

Abstract: A facile and efficient approach for the synthesis of multisubstituted tetrahydropyridazines starting from cyclopropyl ketones and hydrazines has been developed. The transformation is chalcone-based and takes place via a Cloke−Wilson-type rearrangement-involved tandem reaction catalyzed by TfOH in HFIP.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

2025

Publication Types

Select...

Article4

Relationship

Self Cite0

Independent4

Authors

Journals

Cited by 4 publications

References 71 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Synthesis of Bridged Bicyclic Systems peri‐Annulated to the Indole Ring: Tropane‐Fused Indoles

Antropov,

Tokmacheva,

Levina

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

Ytterbium(III) triflate catalysed domino reaction of (3‐formyl‐4‐indolyl)‐derived donor‐acceptor cyclopropane with primary amines provides a simple approach to an unprecedented tetracyclic skeleton in which tropane system is peri‐annulated with an indole core. This process involves the formation of an imine and its (3+2)‐cross‐cycloaddition with donor‐acceptor cyclopropane moiety, yielding indole core under mild reaction conditions. These products are of significant interest for pharmacology as potential hybrid molecules with a dual mode of action.tropane‐fused

show abstract

Synthesis of Bridged Bicyclic Systems peri‐Annulated to the Indole Ring: Tropane‐Fused Indoles

Antropov,

Tokmacheva,

Levina

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Overview of Phenylhydrazine‐Based Organic Transformations

Kushwaha,

Bhardwaj,

Rashi

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

Phenylhydrazines, comprised of a phenyl group attached with hydrazine unit, contribute potentially to organic synthetic transformations. Because of the myriad of synthetic applications, the last decade has witnessed a considerable upsurge of interest to perform various reactions catalyzed/mediated/promoted by phenylhydrazines. Some of these reactions have shown high regioselectivity in short reaction time under mild reaction conditions. The emergence of innumerable synthetic transformations utilizing phenylhydrazine has unleashed numerous openings for the development of diverse heterocyclic scaffolds. Given the synthetic importance of this valuable chemical entity, this review highlights the methodologies utilizing phenylhydrazines. Moreover, the present article will contribute considerably to the organic synthesis as well as in pharmaceutical chemistry. Academically, this review article will be interesting and informative for the researchers attempting to develop new synthetic routes for the heterocyclic structures.

show abstract

Advances in the synthesis of functionalized tetrahydropyridazines from hydrazones

Yu,

Pan

2024

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Chalcone-Based Synthesis of Tetrahydropyridazines via Cloke–Wilson-Type Rearrangement-Involved Tandem Reaction between Cyclopropyl Ketones and Hydrazines

Cited by 4 publications

References 71 publications

Synthesis of Bridged Bicyclic Systems peri‐Annulated to the Indole Ring: Tropane‐Fused Indoles

Synthesis of Bridged Bicyclic Systems peri‐Annulated to the Indole Ring: Tropane‐Fused Indoles

Overview of Phenylhydrazine‐Based Organic Transformations

Advances in the synthesis of functionalized tetrahydropyridazines from hydrazones

Contact Info

Product

Resources

About