Synthesis of 2(3<i>H</i>)-Furanones via Electrophilic Cyclization

Just, Ziwei W.; Larock, Richard C.

doi:10.1021/jo702666j

Cited by 51 publications

(19 citation statements)

References 62 publications

(43 reference statements)

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“…The reaction provided functionallized 2(3H)furanones including spiro-Δ β,γ -butenolides in high yields (Scheme 84). [127] Likewise, ethyl 1-(but-1-yn-1-yl)-1,3-dioxolane-2-carboxylate on reaction with iodine furnished 9-iodo-8-phenyl-1,4,7-trioxaspiro[4,4]non-8-en-6-one in 24 hours afforded 67% yields, while reaction with ICl, accomplished within 4 hours to provide 96% yields (Scheme 85). [127]…”

Section: Synthesis Of Spiro δ βγ -Butenolides By Electrophilic Cyclimentioning

confidence: 99%

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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Spirobutenolides and spirobutyrolactones structural motifs are widespread in various natural products that exhibit a broad array of biological activities. Additionally, their synthetic analogues also serve as biologically active compounds and building blocks of complex molecules. Owing to the wide range of pharmacological activities and structural diversity of the spirobutenolides and spirobutyrolactones, various efficient synthetic methodologies have been established to construct such interesting scaffolds. In the past decades, numerous total syntheses of spirobutenolides and spirobutyrolactones containing natural products have been reported. Structurally diverse spirobutenolides and spirobutyrolactones have been synthesized by using singlet oxygen, Mannich reaction, aldol condensation, rearrangement reaction , Reformatsky reaction, Michael-addition cyclization, Diels-Alder reaction, photocyclization reaction, and pericyclic reactions. Recently, metal-catalyzed cyclization, photocatalyzed radical cyclization, Baylis-Hillman reaction, asymmetric organocatalysis, NHC catalysis, ring contraction reactions, and hypervalent iodine catalysis have emerged as powerful tools to architect these nuclei. This review gives an overview of advancements in chemically and biologically relevant spirobutenolides and spirobutyrolactones of natural and synthetic origin. It also covers the newer methodologies for the construction of natural as well as synthetic spirobutenolides and spirobutyrolactones along with their potential applications.

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Section: Synthesis Of Spiro δ βγ -Butenolides By Electrophilic Cyclimentioning

confidence: 99%

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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“…The reaction afforded the desired substituted 2(3H)-furanones in good to excellent yields (50-98%). 84 Interestingly, in some cases, chlorosubstituted products 171 were observed along with the iodides. The resulting 4-iodo-2(3H)-furanones were further transformed into substituted 2(3H)-furanones by extension of the iodide functionality.…”

Section: Review Syn Thesismentioning

confidence: 99%

Recent Advances in Iodine Monochloride Mediated Electrophilic Cyclizations

Singh

Chimni

2015

Synthesis

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Recent progress in electrophilic cyclizations has led to the development of many electrophilic cyclizing agents. Among them, iodine monochloride (ICl) has recently emerged as one of the most promising. In this Review, we highlight the advances in iodine monochloride mediated electrophilic cyclizations from 2000 to 2014. In addition, the different transformations of organoiodine compounds (the usual products of these electrophilic cyclizations) are discussed.

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“…In the presence of halogen, sulfur and selenium electrophiles, a wide variety of functionally-substituted alkynes undergo electrophilic cyclization to form the corresponding heterocyclic and carbocyclic compounds, including indoles,20 benzofurans,21 benzothiophenes,22 benzoselenophenes,23 benzopyrans,24 furans,25 naphthols,26 naphthalenes,27 isoindolinones,28 coumestans and coumestrols,29 chromones,30 isocoumarins and α-pyrones,31 isochromenes,32 isoquinolines,33 quinolines,34 isoxazoles,35 polycyclic aromatics,36 pyrroles,37 furopyridines,38 furanones,39 and spiro[4,5]trienones 40…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3-Sulfenyl- and 3-Selenylindoles by the Pd/Cu-Catalyzed Coupling of N,N-Dialkyl-2-iodoanilines and Terminal Alkynes, Followed by n-Bu₄NI-Induced Electrophilic Cyclization

et al. 2009

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3-Sulfenyl- and 3-selenylindoles are readily synthesized by a two-step process involving the palladium/copper-catalyzed crossing coupling of N,N-dialkyl-ortho-iodoanilines and terminal alkynes and subsequent electrophilic cyclization of the resulting N,N-dialkyl-ortho-(1-alkynyl)anilines with arylsulfenyl chlorides or arylselenyl chlorides. The presence of a stoichiometric amount of n-Bu4NI is crucial to the success of the electrophilic cyclization. A variety of 3-sulfenyl- and 3-selenylindole derivatives bearing alkyl, vinylic, aryl, and heteroaryl substituents have been prepared in good to excellent yields (up to 99%). By employing N,N-dibenzyl-ortho-iodoanilines, a 3-sulfenyl-N-H-indole has been successfully prepared. In addition, 3-sulfonyl- and 3-sulfinylindoles have also been successfully prepared by facile oxidation of the corresponding 3-sulfenylindoles.

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Synthesis of 2(3H)-Furanones via Electrophilic Cyclization

Abstract: Just, Ziwei W., "Synthesis of 2(3H)-furanones via electrophilic cyclization" (2007). Retrospective Theses and Dissertations. 15078.

Cited by 51 publications

References 62 publications

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Recent Advances in Iodine Monochloride Mediated Electrophilic Cyclizations

Synthesis of 3-Sulfenyl- and 3-Selenylindoles by the Pd/Cu-Catalyzed Coupling of N,N-Dialkyl-2-iodoanilines and Terminal Alkynes, Followed by n-Bu₄NI-Induced Electrophilic Cyclization

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Synthesis of 2(3H)-Furanones via Electrophilic Cyclization

Abstract: Just, Ziwei W., "Synthesis of 2(3H)-furanones via electrophilic cyclization" (2007). Retrospective Theses and Dissertations. 15078.

Cited by 51 publications

References 62 publications

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Recent Advances in Iodine Monochloride Mediated Electrophilic Cyclizations

Synthesis of 3-Sulfenyl- and 3-Selenylindoles by the Pd/Cu-Catalyzed Coupling of N,N-Dialkyl-2-iodoanilines and Terminal Alkynes, Followed by n-Bu4NI-Induced Electrophilic Cyclization

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About

Synthesis of 3-Sulfenyl- and 3-Selenylindoles by the Pd/Cu-Catalyzed Coupling of N,N-Dialkyl-2-iodoanilines and Terminal Alkynes, Followed by n-Bu₄NI-Induced Electrophilic Cyclization