Synthesis of Polycyclic δ-Lactams with Bridged Benzomorphan Skeleton: Selectivity and Diversity Driven by Substituents

Sośnicki, Jacek G.; Idzik, Tomasz J.; Borzyszkowska, Aleksandra; Maciejewska, Gabriela; Struk, Łukasz

doi:10.1021/acs.joc.7b02509

Cited by 6 publications

(24 citation statements)

References 47 publications

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“…Most recently, Sośnicki and co‐workers reported an efficient method for the synthesis of bromo‐functionalized 2,6‐methano‐ and 1,5‐methano‐benzomorphanones ( 52 and 53 ), the core skeleton found in ( R )‐pentazocine, a clinically used drug for analgesic purposes (Scheme ), via an intramolecular bromiranium ion‐induced Friedel–Crafts‐type cyclization from the lactams 50 and 51 , respectively. After a screening of various halogen sources and phosphines as Lewis base catalysts, NBS (1.5 equiv.)…”

Section: Reaction Classesmentioning

confidence: 99%

Stereoselective Haliranium, Thiiranium and Seleniranium Ion‐Triggered Friedel–Crafts‐Type Alkylations for Polyene Cyclizations

Maji

2019

Adv Synth Catal

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Ther eview is aimeda tdescribingt he advances in electrophilic "iranium" ion-triggered Friedel-Crafts-type alkylation for polyenec yclizations. Owing to the greatp otential of halo-, seleno-and sulfeno-functionalized Friedel-Crafts alkylated compounds,n umerous catalytic methodsh aveb een developed in either racemico re nantiopure forms. More importantly,t hese arene-alkylated or polyenecyclized productsc ontaining halo,s eleno ands ulfeno functionality couldb eu seful in further synthetic planning to access biologically active molecules and natural productsw ith highly complex architectures. Starting from aw ide range of classicalL ewis acids, Brønsted acids and Lewis bases through to the very recently developed halogen bondc atalysts (XB-cat.), selenonium cations as Lewis acids etc. are utilized to access these types of compounds.M orer ecently, some of the co-operative catalytic systems such as phosphite-thiourea, sulfonic acid-phosphoramidite, sulfonic acid-selenophosphoramide,s ulfonic acidanion binding thiourea, etc. catalyzing highly diastereo-and enantioselective polyene cyclizations have also been described. Thec onfigurational stability,r eactivity and selectivity of three-membered cationic

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Section: Reaction Classesmentioning

confidence: 99%

Stereoselective Haliranium, Thiiranium and Seleniranium Ion‐Triggered Friedel–Crafts‐Type Alkylations for Polyene Cyclizations

Maji

2019

Adv Synth Catal

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“…Thus, in the next attempt, the N–Me derivative 1a was simply converted into thioanalog 2a in high yields and was then submitted to react with NaBH 4 (25 equiv) and NiCl 2 ·6H 2 O (8.5 equiv) in THF/MeOH (1:1) solution for 15 min at 0 °C and next for 90 min at rt. Under these conditions, the formation of sole indeno[2,1- c ]piperidine product 4a was observed, and this product was isolated in 64% yield (Table , entry 1).…”

Section: Resultsmentioning

confidence: 99%

“…In our previous studies on the synthesis of polycyclic compounds built on the piperidine framework, we designed a convenient synthesis of the novel cyclopropane-fused benzomorphanone derivatives with an internal azabicyclo[4.1.0]heptane unit ( 1 , Scheme ). Their synthesis included the additions of benzylmagnesiates to simple, commercially available 2-pyridones and the halocarbocyclization process followed by intramolecular cyclopropanation of 11-bromo-benzomorphanones using t -BuOK as a base …”

Section: Introductionmentioning

confidence: 99%

Diversity-Oriented Synthesis toward Fused and Bridged Benzobicyclic Piperidin(on)es

2019

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An efficient diverse synthesis of cis-fused indenopiperidines and bridged benzomorphanones, starting from cyclopropane-fused benzomorphanothiones and benzomorphanones, respectively, using NaBH4/NiCl2·6H2O/EtOH as a reducing system, is described. High rigidity of substrates allowed axially controlled syntheses of their trans-mono-alkylated derivatives, subsequently enabling access to both trans-alkyl-functionalized benzobicyclic piperidin(on)es. Diversity-oriented synthesis of naphthalene ring-containing fused naphthoindenopiperidines and bridged naphthomorphanone directly from 2-pyridones was also performed.

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“…In 2018 Sośnicki and co-workers synthesized bromofunctionalized 2,6-methanobenzomorphanones 228 132 starting from the addition of benzylmagnesate 226 to Nsubstituted 2-pyridones P-110, which, in contrast to the above described addition of a Grignard reagent (Scheme 82), delivered mainly 6-benzyl-3,6-dihydro-2-pyridones 227 (Scheme 83). 133 These were cyclized to give 11-bromobenzomorphanones 228 using NBS in nitromethane in the presence of triphenyl phosphite.…”

Section: J G Sośnicki T J Idzikmentioning

confidence: 99%

Pyridones – Powerful Precursors for the Synthesis of Alkaloids, Their Derivatives, and Alkaloid-Inspired Compounds

Sośnicki¹,

Idzik²

2019

Synthesis

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2-Pyridone is characterized by a very wide range of reactivity of a different nature, ranging from electrophilic aromatic substitution, CH–metal-mediated reactions, and NH/OH functionalization of both possible lactam/lactim tautomers, through cycloaddition, to nucleophilic addition and transformation of the tautomeric C=O/C–OH moiety. The high availability of 2-pyridones and the possibility of their far-reaching functionalization additionally increased their values. Therefore, they are very useful building blocks for the synthesis of structurally diverse piperidine and pyridine compounds, including naturally occurring 2-pyridones. This review reports on the use of simple 2-pyridones in the synthesis of alkaloids and alkaloids-inspired compounds based on the piperidine or pyridine framework.1 Introduction2 Structure, Availability, and Reactivity of 2-Pyridones3 Monocyclic Piperidine Alkaloids from 2-Pyridones4 Polycyclic Alkaloids, Their Derivatives, and Alkaloid-Inspired Compounds from 2-Pyridones4.1 New Ring Formation Involving C/N Atoms of the 2-Pyridone Ring4.1.1 Indolizine-Fused 2-Pyridones: Camptothecins and Related Compounds4.1.2 Other Indolizines from 2-Pyridones4.1.3 Compounds Bearing the Quinolizine Ring System4.2 New Ring Formation Involving C/C Atoms of the 2-Pyridone Ring4.2.1 C-2/C-3 Ring Fusion4.2.2 C-3/C-4 Ring Fusion4.2.3 C-4/C-5 Ring Fusion4.2.4 C-5/C-6 Ring Fusion4.2.5 C-2/C-4 Ring Bridge4.2.6 C-2/C-6 Ring Bridge4.2.7 C-3/C-5 Ring Bridge4.2.8 C-3/C-6 Ring Bridge4.2.9 C-4/C-6 Ring Bridge5 Conclusion

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Synthesis of Polycyclic δ-Lactams with Bridged Benzomorphan Skeleton: Selectivity and Diversity Driven by Substituents

Cited by 6 publications

References 47 publications

Stereoselective Haliranium, Thiiranium and Seleniranium Ion‐Triggered Friedel–Crafts‐Type Alkylations for Polyene Cyclizations

Stereoselective Haliranium, Thiiranium and Seleniranium Ion‐Triggered Friedel–Crafts‐Type Alkylations for Polyene Cyclizations

Diversity-Oriented Synthesis toward Fused and Bridged Benzobicyclic Piperidin(on)es

Pyridones – Powerful Precursors for the Synthesis of Alkaloids, Their Derivatives, and Alkaloid-Inspired Compounds

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