A [3+3] Annelation Approach to Tetrahydropyridines

Pattenden, Lisa C.; Wybrow, Robert A. J.; Smith, Stephen A.; Harrity, Joseph P. A.

doi:10.1021/ol0610789

Cited by 43 publications

(11 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…They further broadened the scope of the [3 + 3]-annulation strategy by employing Büchi Grignard reagent for the synthesis of tetrahydropyridines (382-385) [167]. When a series of N-activated aziridines 376 were subjected to addition reaction with dioxolane-based Grignard reagent 380, the corresponding ringopened products 381 were formed in good yields.…”

Section: Synthesis Of Six-membered Rings From Activated Aziridines Anmentioning

confidence: 99%

Ring Expansions of Activated Aziridines and Azetidines

Ghorai

Bhattacharyya

Das

et al. 2015

Topics in Heterocyclic Chemistry

View full text Add to dashboard Cite

Facile construction of small and normal-sized, or more precisely, four to seven-membered aza-heterocyclic ring systems is always a challenging yet rewarding task for the synthetic organic chemists. Fortunately, activated aziridines and azetidines provide a direct and convenient access to this coveted molecular architectures through several elegant ring-expansion approaches. This chapter presents some of the illustrative and contemporary examples to demonstrate the synthetic diversity and efficiency of the ring-expansion strategies of activated aziridines and azetidines towards a vast array of small to normal-sized aza-heterocyclic moieties.

show abstract

Section: Synthesis Of Six-membered Rings From Activated Aziridines Anmentioning

confidence: 99%

Ring Expansions of Activated Aziridines and Azetidines

Ghorai

Bhattacharyya

Das

et al. 2015

Topics in Heterocyclic Chemistry

View full text Add to dashboard Cite

show abstract

“…15 Regioselective bromination of 10 was accomplished with elemental bromine and Hunig’s base to give the key bromide intermediate 11 . 16,17 …”

Section: Resultsmentioning

confidence: 99%

Identification of a 2-phenyl-substituted octahydrobenzo[f]quinoline as a dopamine D3 receptor-selective full agonist ligand

Clark

McCorvy

Conley

et al. 2012

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

This work describes the identification of a novel class of octahydrobenzo[f]quinolines as dopamine D3-selective full agonists. We developed a facile method that utilizes Suzuki coupling for easy incorporations of various substituted pendant rings into the scaffold. A small focused library of octahydrobenzo[f]quinolines 5 was synthesized, and these compounds demonstrated at least 14-fold D2-like selectivity over D1 in native porcine striatal tissue. Furthermore, n-propyl analog 5f was found to be a high affinity (ki = 1.1 nM) D3 dopamine full agonist with 145-fold selectivity over the D2 receptor and about 840-fold selectivity over the D1 receptor. 1.

show abstract

“…Cyclic enamines bearing an electron‐withdrawing protecting group on nitrogen, such as ene‐sulfonamide 1 a , have been shown to be useful precursors to oxygenated piperidines by hydroboration–oxidation, epoxidation‐ring opening and by dihydroxylation . This chemistry has been used in this laboratory for the stereoselective synthesis of pseudoconhydrine, azimic acid, and 5‐hydroxysedamine .…”

Section: Introductionmentioning

confidence: 99%

Platinum‐Catalysed Ring‐Opening Isomerisation of Piperidine Cyclopropanes

2018

View full text Add to dashboard Cite

Ar ange of cyclopropyl-fused N-tosyl piperidines have been synthesised ands hown to undergo ring-opening isomerisation on treatment with platinum(II) catalysts. The products can have either an endo-cyclic or exo-cyclic double bond. The selectivity is influenced by reaction temperature, solventa nd, most significantly,t he catalyst. Am echanism in-volvingC ÀCb ond activation and b-hydride eliminationi s proposed. When b-hydride elimination is blocked, as tereospecific platinum-driven Wagner-Meerwein shift is observed.

show abstract

A [3+3] Annelation Approach to Tetrahydropyridines

Cited by 43 publications

References 19 publications

Ring Expansions of Activated Aziridines and Azetidines

Ring Expansions of Activated Aziridines and Azetidines

Identification of a 2-phenyl-substituted octahydrobenzo[f]quinoline as a dopamine D3 receptor-selective full agonist ligand

Platinum‐Catalysed Ring‐Opening Isomerisation of Piperidine Cyclopropanes

Contact Info

Product

Resources

About