Nucleophilic ring-opening reactions of trans-2-aroyl-3-aryl-cyclopropane-1,1-dicarboxylates with hydrazines

Sathishkannan, Gopal; Tamilarasan, V. John; Srinivasan, Kannupal

doi:10.1039/c6ob02552h

Cited by 21 publications

(7 citation statements)

References 45 publications

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“…Srinivasan and co-workers reported in 2017 the nucleophilic ring opening of trans -2-aroyl-3-arylcyclopropane-1,1-dicarboxylates with arylhydrazine to give dihydropyrazoles and cyclopropane-fused pyridazinones. 28a In 2021, they also observed that trans -2-aroyl-3-arylcyclopropane-1,1-dicarboxylate underwent ring-opening in the presence of naphthylamines and Sc(OTf) 3 to yield dibenzo[ c , h ]acridines. 28b…”

Section: Synthesis Of Nitrogen Heterocyclesmentioning

confidence: 99%

Synthesis of Heterocycles from Donor-Acceptor Cyclopropanes: A Five-Year Recap

Deepthi¹,

Meenakshy²,

Mohan³

2023

Synthesis

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The utility of donor-acceptor cyclopropanes (DACs) for the construction of heterocycles is discussed here. In addition to (3+2), (3+3) and (4+3) cycloaddition pathways, nucleophilic ring-opening reactions, intramolecular transformations and cycloisomerizations in presence of suitable catalysts pave way for the generation of heterocycles from DACs. Mild reactions conditions employed and the variety of starting materials that can be used as reaction partners makes the DAC route for heterocycle synthesis attractive. The literature from 2018-2023 is categorized as below. 1 Introduction 2 Synthesis of Nitrogen heterocycles 2.1 By annulations with anthranils and azadienes 2.2 By nucleophilic attack of anilines and hydrazones 2.3 By reaction with ureas and thioureas 2.4 By annulation reactions using azomethine imine 2.5 By reaction with other N-heterocycles 2.6 By other transformations 3 Synthesis of Oxygen heterocycles 3.1 By intramolecular transformations 3.2 By intermolecular reactions 4 Synthesis of Sulphur/Selenium heterocycles 4.1 By reaction with thiocarbonyl substrates 4.2 By reaction with thio/selenocyanates and thiosulfonate salts 5 Synthesis of N-S/O heterocycles 6 Conclusions

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Section: Synthesis Of Nitrogen Heterocyclesmentioning

confidence: 99%

Synthesis of Heterocycles from Donor-Acceptor Cyclopropanes: A Five-Year Recap

Deepthi¹,

Meenakshy²,

Mohan³

2023

Synthesis

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“…reported the reaction of trans ‐2‐aroyl‐3‐arylcyclopropane‐1,1‐dicarboxylate 105 with arylhydrazines in refluxing EtOH for the synthesis of dihydropyrazole derivatives 106 in moderate to excellent yields. On reactions with hydrazine in refluxing AcOH, the authors obtained the cyclopropane‐fused pyridazinone derivatives 107 (Scheme ) . These reactions showed compatibility with a variety of substituted hydrazine and DACs.…”

Section: Synthesis Of Six‐membered Nitrogen Heterocyclesmentioning

confidence: 99%

Donor–Acceptor Cyclopropanes as an Expedient Building Block Towards the Construction of Nitrogen‐Containing Molecules: An Update

et al. 2020

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Nitrogen‐containing molecules are the key structural constituent of many pharmaceutical compounds that play a pivotal role in drug development. Owing to their multifaceted medicinal importance, several synthetic approaches have been delineated in the recent past for their construction. Over the past few decades the augmented use of donor–acceptor cyclopropanes (DACs) as three‐carbon synthetic equivalents, despite their ring strain, for the construction of innumerable hetero‐ and carbocycles of pharmaceutical importance has raised the interest of synthetic chemists to this topic. Owing to their zwitterionic nature due to the vicinal disposition of donor and acceptor groups, they have been frequently used in ring‐opening reactions, cycloadditions, and rearrangements. This review is mainly focused on assorted reactions of DACs with various nitrogen‐containing dipolarophiles like imines, azides, cyanates, isothiocyanates, nitrosocarbonyls, hydrazines, diaziridines, triazinanes, diazenes, etc. towards the synthesis of nitrogen‐containing molecules of pharmaceutical and industrial importance. This review is in continuation of our review published in the Israel Journal of Chemistry in April 2016, and includes the literature from April 2016 to May 2019.

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“…135 Hence, pyrazolines 161 were produced in high yields. At the same time, the reaction of 160a with an unsubstituted hydrazine immediately yielded pyrazole 157a.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles

et al. 2017

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Ring opening of donor-acceptor cyclopropanes with variousN-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor-acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.

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Nucleophilic ring-opening reactions of trans-2-aroyl-3-aryl-cyclopropane-1,1-dicarboxylates with hydrazines

Cited by 21 publications

References 45 publications

Synthesis of Heterocycles from Donor-Acceptor Cyclopropanes: A Five-Year Recap

Synthesis of Heterocycles from Donor-Acceptor Cyclopropanes: A Five-Year Recap

Donor–Acceptor Cyclopropanes as an Expedient Building Block Towards the Construction of Nitrogen‐Containing Molecules: An Update

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles

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Nucleophilic ring-opening reactions of trans-2-aroyl-3-aryl-cyclopropane-1,1-dicarboxylates with hydrazines

Cited by 21 publications

References 45 publications

Synthesis of Heterocycles from Donor-Acceptor Cyclopropanes: A Five-Year Recap

Synthesis of Heterocycles from Donor-Acceptor Cyclopropanes: A Five-Year Recap

Donor–Acceptor Cyclopropanes as an Expedient Building Block Towards the Construction of Nitrogen‐Containing Molecules: An Update

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes

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Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles