<i>Diels‐alder</i> reaction of thebaine via <i>N</i>‐formylnorthebaine with nitroethene; reduction of the nitro group in 7α‐nitroethenoisomorphinans (chemistry of opium alkaloids, part XX)

Maat, L.; Peters, Joop A.; Prazeres, M. A.

doi:10.1002/recl.19851040705

Cited by 14 publications

(2 citation statements)

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“…To diminish the basicity of the alkaloid, a formyl group was introduced in position N 17 . When N 17 -formyl-northebaine (9a) was heated with the same dienophile (in benzene, boiling for 19 h), the cycloaddition took place successfully [40].…”

Section: Reactions Of ∆ 68 -Morphinandienes Thebainementioning

confidence: 99%

Diels–Alder Adducts of Morphinan-6,8-Dienes and Their Transformations

et al. 2022

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6,14-ethenomorphinans are semisynthetic opiate derivatives containing an ethylene bridge between positions 6 and 14 in ring-C of the morphine skeleton that imparts a rigid molecular structure. These compounds represent an important family of opioid receptor ligands in which the 6,14-etheno bridged structural motif originates from a [4 + 2] cycloaddition of morphinan-6,8-dienes with dienophiles. Certain 6,14-ethenomorphinans having extremely high affinity for opioid receptors are often non-selective for opioid receptor subtypes, but this view is now undergoing some revision. The agonist 20R-etorphine and 20R-dihydroetorphine are several thousand times more potent analgesics than morphine, whereas diprenorphine is a high-affinity non-selective antagonist. The partial agonist buprenorphine is used as an analgesic in the management of post-operative pain or in substitution therapy for opiate addiction, sometimes in combination with the non-selective antagonist naloxone. In the context of the current opioid crisis, we communicated a summary of several decades of work toward generating opioid analgesics with lesser side effects or abuse potential. Our summary placed a focus on Diels–Alder reactions of morphinan-6,8-dienes and subsequent transformations of the cycloadducts. We also summarized the pharmacological aspects of radiolabeled 6,14-ethenomorphinans used in molecular imaging of opioid receptors.

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Section: Reactions Of ∆ 68 -Morphinandienes Thebainementioning

confidence: 99%

Diels–Alder Adducts of Morphinan-6,8-Dienes and Their Transformations

et al. 2022

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“…[69,73,74]. Therefore, thebaine is long known to take part in Diels-Alder reactions as it was reported in some studies [75,76,77].…”

Section: Pharmacologymentioning

confidence: 99%

Opium and Its Major Alkaloidal Constituents: A Review Article

Khan¹,

Bala²,

Pathania³

et al. 2022

YMER

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Poppy (Papaver somniferous L.) is a member of the Papaveraceous family. It is indigenous ofsouth east of Europe and Asia. It is cultivated all over the world and there is not any wild type of this species. It is widely grown as an ornamental flower throughout Europe, North America, South America, and Asia. Until now more than 40 different alkaloids have been known in thisspecies which the most important ones are morphine, codeine, thebaine, papaverine and noscapine. Alkaloids are affected with genetical characteristics and environmental conditions. Poppy seeds are an important food item and the source of poppy seed oil, healthy edible oilthat has many uses. The most important application of papaver alkaloids is due to their analgesic properties. Use of opium poppy (Papaver somniferum L.) as a medicinal plant hasbeen described in the ancient literature of Indian system of medicine (Ayurveda). Keyword: - Opium, Alkaloids, Morphine, Codeine, Medicinal plants

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TheNef Reaction

Pinnick

1990

Organic Reactions

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The Nef reaction is usually defined as the conversion of a primary or secondary nitroalkane into the corresponding carbonyl compound. This reaction was reported by the Swiss chemist J. U. Nef in 1894. Hydrochloric and sulfuric acid give the same result. The conversion of a nitro group to a carbonyl group has become an important synthetic tool because of the ease of preparation of substituted nitro compounds by condensation of nitroalkanes with aldehydes (the Henry reaction), conjugate addition of nitroalkanes to electrophilic alkenes, or carbon alkylation of the dianion of primary nitroparaffins. The Nef reaction is one of the better examples of “umpolung” reactivity in which the original nitro compound anion functions as an acyl anion equivalent. This chapter discusses the Nef reaction and modifications of the original process that extend the variety of compounds which are useful as substrates. Each modification is considered according to general mechanistic type and is organized in a “reagent” approach. The Tabular Survey lists all known examples of both the Nef reaction and these modifications so that specific comparison of methods can be made.

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Diels‐alder reaction of thebaine via N‐formylnorthebaine with nitroethene; reduction of the nitro group in 7α‐nitroethenoisomorphinans (chemistry of opium alkaloids, part XX)

Cited by 14 publications

References 14 publications

Diels–Alder Adducts of Morphinan-6,8-Dienes and Their Transformations

Diels–Alder Adducts of Morphinan-6,8-Dienes and Their Transformations

Opium and Its Major Alkaloidal Constituents: A Review Article

TheNef Reaction

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