Synthesis of the Benzo-fused Indolizidine Alkaloid Mimics

Comins, Daniel L.; Higuchi, Kazuhiro

doi:10.1186/1860-5397-3-42

Cited by 13 publications

(11 citation statements)

References 24 publications

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“…Based on the above results and the published literature [ 32 , 33 , 34 , 35 ], we postulated a tentative mechanism of halogen–metal exchange in Scheme 3 . Initially, we used one equiv.…”

Section: Resultssupporting

confidence: 58%

Halogen–Metal Exchange on Bromoheterocyclics with Substituents Containing an Acidic Proton via Formation of a Magnesium Intermediate

Tian¹,

Shang²,

Wang³

et al. 2017

Molecules

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A selective and practical bromine–metal exchange on bromoheterocyclics bearing substituents with an acidic proton under non-cryogenic conditions was developed by a simple modification of an existing protocol. Our protocol of using a combination of i-PrMgCl and n-BuLi has not only solved the problem of intermolecular quenching that often occurred when using alkyl lithium alone as the reagent for halogen–lithium exchange, but also offered a highly selective method for performing bromo–metal exchange on dibrominated arene compounds through chelation effect.

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“…Based on the above results and the published literature [ 32 , 33 , 34 , 35 ], we postulated a tentative mechanism of halogen–metal exchange in Scheme 3 . Initially, we used one equiv.…”

Section: Resultssupporting

confidence: 58%

Halogen–Metal Exchange on Bromoheterocyclics with Substituents Containing an Acidic Proton via Formation of a Magnesium Intermediate

Tian¹,

Shang²,

Wang³

et al. 2017

Molecules

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“…Oxohydropyridines, one class of the cyclization products of N-substituted b-amino acids, are very important intermediates in the synthesis of a large number of biologically active heterocyclic compounds [14,15]. Many approaches to their synthesis have been developed [16][17][18][19][20][21]. Oxohydropyridines can also be used as precursors in the stereoselective synthesis of substituted [22] or disubstituted b-amino acids [23].…”

Section: Introductionmentioning

confidence: 99%

Unexpected transformation of ethyl 1-(4-chlorophenyl)-2-methyl-4-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate and antibacterial activity of the products

et al. 2014

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The cyclization reaction of N-(4-chlorophenyl)-b-alanine, in the presence of piperidine as a catalyst, provided ethyl 1-(4-chlorophenyl)-2-methyl-4-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate, which reactions with different hydrazines were carried out resulting in formation of a variety of tetrahydropyridine, dihydropyrazolone, and oxazole derivatives in good yields. 5-[2-[(4-Chlorophenyl) amino]ethyl]-4-(1-hydrazinylethylidene)-2,4-dihydro-3H-pyrazol-3-one was converted into a series of hydrazones, which provided tetrahydro-3H-pyrazolo[4,3-c]pyridin-3-one under treatment with acids. The structures of all synthesized compounds were confirmed by IR, 1 H NMR, and 13 C NMR spectroscopy. The structures of three compounds were unambiguously assigned by means of X-ray analysis data. Some of the synthesized compounds exhibited weak antibacterial activity.

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“…Natural piperidine alkaloids embody hydropyridone moiety in their structure. Compounds containing this moiety are important intermediates in the synthesis of other biologically active heterocyclic compounds , such as piperidines , perhydroquinolines , and indolizidines .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Heterocyclization of 1‐Aryl‐2‐methyl‐4‐oxo‐1,4,5,6‐tetrahydropyridine‐3‐carboxylates

Sapijanskaitė

Mickevičienė

Kantminienė

et al. 2017

Journal of Heterocyclic Chem

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A series of novel isoxazole, dihydropyrazolone, and tetrahydropyridine derivatives were synthesized by the reaction of corresponding ethyl 1‐substituted aryl‐2‐methyl‐4‐oxo‐1,4,5,6‐tetrahydropyridine‐3‐carboxylates with different hydrazines and hydroxylamine. Reaction of tetrahydropyridone with N,N‐dimethylformamide dimethyl acetal provided 1‐(5‐chloro‐2‐methylphenyl)‐2‐[2‐(dimethylamino)ethenyl]‐4‐oxo‐1,4,5,6‐tetrahydropyridine‐3‐carboxylate, which was cyclized into a bicyclic compound on treatment with ammonium acetate. The structures of all synthesized compounds were confirmed by IR, 1H NMR, and 13C NMR spectroscopy data. The structure of 5‐(5‐chloro‐2‐methylphenyl)‐4‐methyl‐2‐phenyl‐2,5,6,7‐tetrahydro‐3H‐pyrazolo[4,3‐c]pyridin‐3‐one was unambiguously assigned by means of X‐ray analysis data.

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Synthesis of the Benzo-fused Indolizidine Alkaloid Mimics

Cited by 13 publications

References 24 publications

Halogen–Metal Exchange on Bromoheterocyclics with Substituents Containing an Acidic Proton via Formation of a Magnesium Intermediate

Halogen–Metal Exchange on Bromoheterocyclics with Substituents Containing an Acidic Proton via Formation of a Magnesium Intermediate

Unexpected transformation of ethyl 1-(4-chlorophenyl)-2-methyl-4-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate and antibacterial activity of the products

Synthesis and Heterocyclization of 1‐Aryl‐2‐methyl‐4‐oxo‐1,4,5,6‐tetrahydropyridine‐3‐carboxylates

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