Regioselective Nitrative Cyclization of 1,6-Enynes with <i>t</i>-BuONO under Metal-Free Conditions

Wei, Wanzhi; Ying, Wei‐Wei; Bao, Wenhui; Gao, Le‐Han; Xu, Xudong; Meng, Xiaoxiao; Chen, Gan-Ping; Li, Qiang

doi:10.1021/acssuschemeng.8b03752

Cited by 37 publications

(19 citation statements)

References 62 publications

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“…The scale-upe xperiment shows the practical utility of the presentm ethodology.T he desired product was further reduced to an amine group using Zn-AcOH. [92] In 2019, Fan and co-workers reported the cascade synthesis of nitrocyclobutane-fusedn aphthalene-1,2-diones (88)b yr eacting TBN and benzene-linked allenynes (87)u nder am etal-free condition (Scheme 62). [93] In the proposed mechanism initially [2+ +2] cycloaddition generates an intermediate When the identical reactionw as carried out in an oxidantfree and in the presence of alcohola nd amine the desired product obtained was 5-oxo-2H-benzo[g]indole-1-oxides/functionalized naphthalene-1,2-diones, respectively.T he benzoindole-1-oxides products can be transformed into 1H-benzo[g]indol-5-ol derivatives which are significant in pharmaceuticals.…”

Section: Nitrationmentioning

confidence: 99%

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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The upsurge interesti nt he development of efficient methodologies for the constructiono fn itrogen-containing frameworks via the use of expedient reagents have been creating ar enaissance in contemporary organic chemistry.I nt his perspective, tertbutyl nitrite (TBN) is an emerging building block. Due to its uniques tructuralf eatures, it shows differential reactivity under different reaction conditions. These diverse reactivities have resulted in the construction of ad iverse array of complex N-containing molecules. The primary objective of the presentr eview is to bring the latest findings of TBN in terms of its applications in reactions (oxidation, diazotization, nitrosation, nitration, oximation, N-synthon, and miscellaneous reactions) into the limelight.F or simplicity and brevity,r eactions in each section are explained with the mechanism of formation and selected examples are given.Scheme1.Differential reactivity of TBN. 4455 MinireviewScheme4.Visible-light-promoted synthesis of selenide ethers.Scheme5.Proposed mechanism for visible-light-promoted synthesis of selenide ethers.Scheme6.TBN-mediated synthesis of selenide ethers.Scheme7.Metal-free synthesis of 4-carbonylquinolines.Scheme8.Proposed mechanism for synthesis of 4-carbonylquinolines.Scheme9.TBN-mediated demethylative borylation of methylarenes.Scheme10. Plausible mechanism for demethylative borylation of methylarenes.Scheme11. Trifluoromethylation of various aromatic amine substrates.Scheme12. Copper-catalyzed isoperfluoropropylation of anilines.Scheme13. Plausible mechanism for Cu-catalyzed isoperfluoropropylation of anilines.Scheme14. TBN-mediateddiazotizative allylation of aromatic amines.Scheme15. Oxidativecyanomethylationo fa lkenes via CÀHb ond activation.Scheme16. TBN-mediatedand Cu-catalyzedsynthesis of thioether.

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Section: Nitrationmentioning

confidence: 99%

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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“…On the basis of these mechanistic studies and literature reports, we propose herein a plausible mechanism for this azidation cyclization in Scheme . At the beginning, an azide radical is generated by oxidation of TMSN 3 in the presence of K 2 S 2 O 8 .…”

Section: Methodsmentioning

confidence: 71%

“…In addition, the above azidation is usually accompanied by annulation, which limits the diversity of the products. Very recently, we have established a regioselective nitration cyclization of 1,6‐enynes with t ‐BuONO . In our eﬀorts to extend the utility of this process, we became interested in developing regioselective azidation cyclization of 1,6‐enynes.…”

Section: Methodsmentioning

confidence: 99%

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Potassium‐Persulfate‐Promoted Regioselective Azidation/Cyclization of 1,6‐Enynes

Fang²,

Gao

et al. 2019

Asian J Org Chem

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An efficient, environmentally benign and sustainable method for the synthesis of 2-pyrrolidinones from 1,6enynes via an unusual regioselective azidation/cyclization is described. The products have been obtained in good yields without the assistance of any transition-metal catalysts or ligands. To demonstrate the utility of this protocol, the azidation products are converted to a synthetically valuable amine or triazole. This azidation cyclization involves a radical process, allows a regioselective way toward the formation of one CÀ N bond and one CÀ C bond.

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“…On the basis of the above experimental results and previous studies, a plausible mechanism was proposed in Scheme . NO 2 radical was generated form a series of reactions based on the combination of tert ‐butyl nitrite ( t ‐BuONO, 3 a ) with trace O 2 and H 2 O under heating condition . As that was proved via DFT study by Patel et al, the attacking of .…”

Section: Methodsmentioning

confidence: 99%

Mild and Regioselective Three‐component Heteroarylation‐Nitration of Alkenes with Imidazo[1,2‐a]pyridines and tert‐Butyl Nitrite

et al. 2020

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An efficient and regioselective threecomponent heteroarylation-nitration of alkenes with imidazo[1,2-a]pyridines and tert-butyl nitrite has been developed. The process tolerants a variety of functional groups under mild conditions in the absence of catalysts and additives to give nitro functionalized imidazo[1,2-a]pyridine derivatives in moderate to good yields. The reaction is also applicable for some other aza-heterocycles.

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Regioselective Nitrative Cyclization of 1,6-Enynes with t-BuONO under Metal-Free Conditions

Cited by 37 publications

References 62 publications

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Potassium‐Persulfate‐Promoted Regioselective Azidation/Cyclization of 1,6‐Enynes

Mild and Regioselective Three‐component Heteroarylation‐Nitration of Alkenes with Imidazo[1,2‐a]pyridines and tert‐Butyl Nitrite

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