Triphenylphosphine-mediated reaction of dialkyl azodicarboxylate with activated alkenes leading to pyrazolines

Yamazaki, Shoko; Maenaka, Yuta; Fujinami, Ken; Mikata, Yuji

doi:10.1039/c2ra21249h

Cited by 16 publications

(3 citation statements)

References 68 publications

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“…Recent reported articles on annulations with zwitterions have given access to functionalized N ‐carboxylate pyrazolines. Yamazaki et al [93a] . investigated the cycloaddition reaction between Huisgen zwitterions 283 and electron‐deficient alkenes 284 toward 3‐alkoxy pyrazolines 285 , with no diastereoselectivity (Scheme 59a).…”

Section: Annulations Using Huisgen Zwitterionsmentioning

confidence: 99%

Strategies and Methods for the Synthesis of 2‐Pyrazolines: Recent Developments (2012–2022)

Matiadis

2023

Adv Synth Catal

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2‐Pyrazolines are important five‐membered heterocycles, containing two adjacent nitrogen atoms. They can incorporate various functional groups and possess unique biological properties. Moreover, they have been used as useful building blocks. In recent years, the field of 2‐pyrazoline synthesis has experienced enormous progress. Novel strategies have been developed, and many studies reporting improvements or adaptations of existing protocols have been published, giving access to new functionalizations, unexplored structures, and/or enantioselective synthesis. This review summarizes the progress made in synthetic methodologies during the period from 2012 to 2022. The functionalization challenges and capabilities, scopes and limitations of the reactions, substitution patterns, and mechanisms of the reactions, where appropriate, will be discussed.

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Section: Annulations Using Huisgen Zwitterionsmentioning

confidence: 99%

Strategies and Methods for the Synthesis of 2‐Pyrazolines: Recent Developments (2012–2022)

Matiadis

2023

Adv Synth Catal

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“…Ethenetricarboxylate derivatives have been employed as highly electrophilic CC components in various bond-forming reactions . Ethenetricarboxylates allow facile derivatization at the 2-carboxyl group.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular [2 + 2] and [4 + 2] Cycloaddition Reactions of Cinnamylamides of Ethenetricarboxylate in Sequential Processes

et al. 2016

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Intramolecular [2 + 2] and [4 + 2] cycloaddition reactions of cinnamylamides of ethenetricarboxylate in sequential processes have been studied. Reaction of 1,1-diethyl 2-hydrogen ethenetricarboxylate and trans-cinnamylamines in the presence of EDCI/HOBt/EtN led to pyrrolidine products in one pot, via intramolecular [2 + 2], [4 + 2], and some other cyclizations. The types of the products depend on the substituents on the benzene ring and the reaction conditions. Reaction of cinnamylamines without substituents on the benzene ring and with halogens and OMe on the para position at room temperature gave cyclobutane-fused pyrrolidines as major products via [2 + 2] cycloaddition. The reaction at 80 °C in 1,2-dichloroethane gave δ-lactone fused pyrrolidines as major products, probably via ring-opening of the cyclobutanes. Interestingly, reaction of 1,1-diethyl 2-hydrogen ethenetricarboxylate and cinnamylamines bearing electron-withdrawing groups such as NO, CN, COMe, COEt, and CF on ortho and para positions in the presence of EDCI/HOBt/EtN at room temperature or at 60-80 °C gave tetrahydrobenz[f]isoindolines via [4 + 2] cycloaddition as major products. DFT studies have been performed to explained the observed [2 + 2]/[4 + 2] selectivity.

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“…Among numerous bioactive pyrazolines and pyrazoles, it is noteworthy that a group of 3-oxy(oxo) analogues possess important and diverse properties including antipyretic, analgesic, fungicidal, and anti-inflammatory activities (Figure ). , Under this circumstance, the development of effective synthetic methods for pyrazolines and pyrazoles has therefore stimulated much interest from chemists. − Traditional approaches such as the condensation of 1,3-dicarbonyl compounds with hydrazines and the [3 + 2] cycloaddition of 1,3-dipoles have proven to be effective; however, alternative and efficient synthetic strategies for structurally diverse pyrazolines and pyrazoles remain highly desirable. Over the past decade, great progress in this aspect has been witnessed. , …”

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confidence: 99%

Divergent Reactivity of Nitrocyclopropanes with Huisgen Zwitterions and Facile Syntheses of 3-Alkoxy Pyrazolines and Pyrazoles

Yang

Liu

et al. 2016

Org. Lett.

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A novel annulation reaction of trans-2-substituted-3-nitrocyclopropane-1,1-carboxylates with in situ generated Huisgen zwitterions is reported, providing facile synthesis of 3-alkoxy pyrazolines in good yields and high diastereoselectivities. This reaction unveils the divergent reactivity of the nitrocyclopropanes as a kind of versatile donor-acceptor cyclopropanes. It is also demonstrated that the prepared 3-alkoxy pyrazolines from di-tert-butyl azodicarboxylate can be readily transformed into the corresponding 3-alkoxy 1H-pyrazoles in moderate yields.

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Triphenylphosphine-mediated reaction of dialkyl azodicarboxylate with activated alkenes leading to pyrazolines

Cited by 16 publications

References 68 publications

Strategies and Methods for the Synthesis of 2‐Pyrazolines: Recent Developments (2012–2022)

Strategies and Methods for the Synthesis of 2‐Pyrazolines: Recent Developments (2012–2022)

Intramolecular [2 + 2] and [4 + 2] Cycloaddition Reactions of Cinnamylamides of Ethenetricarboxylate in Sequential Processes

Divergent Reactivity of Nitrocyclopropanes with Huisgen Zwitterions and Facile Syntheses of 3-Alkoxy Pyrazolines and Pyrazoles

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