Aza-Diels-Alder Reaction: An Efficient Approach for Construction of Heterocycles

Sarmah, Manas M.; Prajapati, Dipak

doi:10.2174/1385272819666140529000155

Cited by 16 publications

(7 citation statements)

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“…[41] The aza-Diels-Alder reaction is among the most effective protocols for the preparation of six-membered nitrogenbearing heterocycles, especially in the creation of various biologically relevant small molecules. [41,42]…”

Section: Aza-diels-alder Reactionmentioning

confidence: 99%

Samarium(III) Triflate in Organic Synthesis: a Mild and Efficient Catalyst

Dey

Majhi

2023

ChemistrySelect

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Lanthanides have shown great potential in the field of magnetic materials, telecommunications, hard‐disk drives, catalysis, medicine, agriculture, and more. Recently, lanthanide complexes have gained significant attention in cancer diagnosis and therapy because of the multifunctional chemical and magnetic activities of the lanthanide‐ion 4 f electronic configuration. Among lanthanides, samarium metal and its derivatives have been the subject of many applications in organic transformations. Various metal triflates such as Bi(OTf)3, Yb(OTf)3, In(OTf)3, Sc(OTf)3, Er(OTf)3, Ce(OTf)3, Sm(OTf)3, and others play a profound role in developing novel eco‐friendly protocols in organic synthesis with excellent efficiency and selectivity. Among lanthanide triflate, samarium(III) triflate has a remarkable contribution in synthesizing promising organic molecules as it has been shown to be moisture tolerant and a reusable Lewis catalyst under mild conditions. The present review aims to focus on different useful protocols using samarium(III) triflate as an efficient catalyst for the first time elegantly.

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Section: Aza-diels-alder Reactionmentioning

confidence: 99%

Samarium(III) Triflate in Organic Synthesis: a Mild and Efficient Catalyst

Dey

Majhi

2023

ChemistrySelect

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“…e target scaffold (THN derivatives, X � N) is an aza variant of 1,2,3,4-tetrahydroquinolines (X � CH), a nucleus commonly accessible via Povarov reaction (Scheme 1). e Povarov reaction (aka aza Diels-Alder or imino Diels-Alder) is a three-component reaction between an aromatic amine, an aldehyde, and an alkene in the presence of a Lewis or a Brønsted acid catalyst [15,16]. Povarov chemistry has been extensively utilized to construct several heterocyclic structures especially pyridinefused heterocycles [17].…”

Section: Synthetic Plan Of Target Compoundsmentioning

confidence: 99%

Reexamining Povarov Reaction’s Scope and Limitation in the Generation of HCV-NS4A Peptidomimetics

Khayat

Omar

Elfaky

et al. 2022

Heteroatom Chemistry

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Chronic Hepatitis C is a global health threat and a silent killer. Regardless of the profound progress in preventing and treating this disease, research continues to discover new direct antiviral agents (DAAs), especially against novel targets. Our research has been directed to leverage the NS4A binding site to develop peptidomimetic inhibitors of the hepatitis C virus (HCV) NS3 protease. In previous reports, we could provide evidence of tunability of this site by peptide and nonpeptide NS3/4A inhibitors. In this report, we used structure-based techniques to design 1,2,3,4-tetrahydro-1,7-naphthyridine derivative as NS4A core mimics that cover the region between residues Ile-25′ to Arg-28′. The synthetic plan featured the Povarov reaction as an efficient strategy to construct the 1,7-naphthyridine core. Although this reaction has been reported in many literatures, critical assessments for its scope and limitations are scarce. In our work, we found that Povarov was extremely sensitive to alkene and aldehyde reactants. Moreover, using pyridine amines was not as successful as anilines. The most striking results were the lack of stability of compounds during purification and storage. The four compounds that survived the stability problems (1a-1d) did not show significant binding potency with NS3, because their structures were too simple to resemble the originally planned compounds.

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“…The rhodium-catalyzed reactions of azirines 120 with ortho-fused triazoles, [1][2][3]triazolo[1,5-a]pyridines 118, have been studied in [54] (Scheme 23). The final products of the reaction were previously unknown 4H-pyrido[1,2-a]pyrazine derivatives 122, which resulted from 1,6-electrocyclization of 1-(pyridin-2-yl)-2-azabuta-1,3-dienes 121 (1,4-diazahexa-1,3,5trienes with the terminal C=N bond as part of the pyridine system).…”

Section: 6-electrocyclization Of 1-oxa-4-azahexa-135-trienes To 2h-14-oxazinesmentioning

confidence: 99%

“…Conjugated azapolyenes such as azabuta-1,3-dienes and aza-/diaza-/oxaza-/oxadiazahexa-1,3,5-trienes (Figure 1) are valuable building blocks in the synthesis of a variety of acyclic and heterocyclic nitrogen-containing compounds [1][2][3][4][5]. These highly unsaturated compounds are generally classified into three types: electron-rich, neutral, and electrondeficient azapolyenes.…”

Section: Introductionmentioning

confidence: 99%

Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes

2021

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Conjugated azapolyenes (azabuta-1,3-dienes, aza-/diaza-/oxaza-/oxadiazahexa-1,3,5-trienes) are highly reactive in electrocyclization reactions, which makes them convenient precursors for the synthesis of a wide range of four-, five-, and six-membered nitrogen heterocycles that are of relevance for medicinal chemistry. Ring opening reactions of 2H-azirines and azoles containing an N–N or N–O bond, initiated by a transition metal carbene, have become increasingly important in recent years, since they easily allow the generation of azapolyenes with different numbers of double bonds and heteroatoms in various positions. This review summarizes the literature, published mainly in the last decade, on the synthetic and mechanistic aspects of electrocyclizations of azapolyenes generated by the carbene method.

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Aza-Diels-Alder Reaction: An Efficient Approach for Construction of Heterocycles

Cited by 16 publications

References 0 publications

Samarium(III) Triflate in Organic Synthesis: a Mild and Efficient Catalyst

Samarium(III) Triflate in Organic Synthesis: a Mild and Efficient Catalyst

Reexamining Povarov Reaction’s Scope and Limitation in the Generation of HCV-NS4A Peptidomimetics

Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes

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