De Novo Synthesis of 3-Pyrrolin-2-Ones

Pelkey, Erin T.; Pelkey, Sarah J.; Greger, Jessica G.

doi:10.1016/bs.aihch.2015.04.001

Cited by 24 publications

(21 citation statements)

References 901 publications

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“…The oxidation of pyrrole has the potential to yield 3‐pyrrolin‐2‐ones, however, due to the reactive nature of this molecule it often undergoes decomposition or uncontrolled polymerization under oxidative and acidic conditions. The present review will focus on the oxidation of pyrrole and pyrrole‐containing systems towards 3‐pyrrolin‐2‐ones and related pyrrole systems, and has been categorized according to the oxidizing agent used …”

Section: Introductionmentioning

confidence: 99%

The Oxidation of Pyrrole

Howard

Rihak

Bissember

et al. 2015

Chemistry An Asian Journal

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The dearomatization of heterocycles has been a powerful means for producing functional molecules in synthesis. In the case of pyrroles, reductive methods (such as the Birch reduction) have been most widely exploited, while oxidative methods are generally dismissed as too difficult or unpredictable to be useful. However, since the early twentieth century considerable research has been carried out on the controlled oxidation of pyrroles to give highly functionalized products, using a variety of oxidants. This review presents a summary of all work up until the present day in the area of pyrrole oxidation, looking at the use of peroxide, singlet oxygen, hypervalent iodine reagents, a range or organic and inorganic oxidants, and electrochemical approaches. It also offers some perspective on the potential future role of pyrrole oxidation in synthesis.

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Section: Introductionmentioning

confidence: 99%

The Oxidation of Pyrrole

Howard

Rihak

Bissember

et al. 2015

Chemistry An Asian Journal

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“…4 Both reactivities are complementary, giving access to advanced intermediates for the preparation of biologically relevant aza-heterocycles, found in many alkaloid natural products (Figure 1). 5 In 2015, Pelkey and co-workers 6 compiled the known syntheses of 3-pyrrolin-2-ones 1. Indeed, compounds 1 or 2 can be synthesized by different methods: oxidation of pyrrole (R = H, Me), 7 cyclization (especially for the synthesis of substituted unsaturated -lactams), 8 elimination, 9 via diazo compounds, 10 condensation with 2,5-dimethoxy-2,5-dihydrofuran (5), 11 and metathesis.…”

Section: Scheme 1 Reactivity Of Unsaturated -Lactams 1 Ormentioning

confidence: 99%

N-Acyliminium Ion Chemistry: Improving the Access to Unsaturated γ-Lactams and Their N-α-Methoxylated Derivatives: Application to an Expeditive Synthesis of (±)-Crispine A

Souquet¹,

Drici²,

Fayssal

et al. 2020

Synthesis

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“…In order to establish these useful skeletons, many synthetic methods have been realized. [5] However, alternative procedures are continuing under demand.…”

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confidence: 99%