Stereoselective synthesis of the rat selective toxicant norbormide

Jay-Smith, Morgan; Murphy, Elaine; Shapiro, Lee; Eason, Charles; Brimble, Margaret A.; Rennison, David

doi:10.1016/j.tet.2016.07.014

Cited by 8 publications

(7 citation statements)

References 60 publications

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“…A series of 2‐acylated pyridine N ‐oxides, prepared by this procedure, are shown in Table . 2‐Acyl pyridine N ‐oxide derivatives are known to be important synthetic precursors for the preparation of agrochemical and pharmaceutical products. A silver‐catalyzed decarboxylative acylation of pyridine N ‐oxides by α‐oxocarboxylic acids, which leads to the formation of both C2‐ and C4‐acylated products, has been reported recently …”

Section: Resultsmentioning

confidence: 99%

“…1 2,139.4,136.7,133.1,129.6,129.5,125.7,123.5,36.1,22.7 ppm. MS (EI): m/z (%) = 199 (30) [M] + , 182 (100), 167 (96), 152 (7), 139 (7), 119 (8), 106 (30), 91 (21), 78 (74), 65 (20), 51 (25). C 13 H 13 NO (199.25): calcd.…”

Section: -(4-methylbenzyl) Pyridine 1-oxide (3c)mentioning

confidence: 99%

“…The general procedure was followed by using 4-nitropyridine N-oxide (1 mmol, 2,139.4,138.6,136.2,130.5,128.8,127.8,123.5,119.12,32.0,22.7 ppm. MS (EI): m/z (%) = 244 (44) [M] + , 227 (66), 211 (7), 197 (14), 181 (70), 169 (13), 154 (14), 136 (40), 127 (17), 119 (25), 110 (18) H 4.95, N 11.47; found C 63.67, H 4.95, N 11.49.…”

Section: -(4-methylbenzyl)-4-nitropyridine 1-oxide (3g)mentioning

confidence: 99%

“…The general procedure was followed by using quinoline N-oxide (1 mmol, 145 mg), K 2 S 2 O 8 (1.25 mmol, 338 mg), CuO (12 mg, 15 mol-%), p-Xylene (3 mmol, 0.37 mL), and acetonitrile (2 mL 1,138.4,138.3,137.3,135.2,130.7,129.4,128.8,128.7,127.9,122.7,111.9,116.1,43.5,23.3 ppm. MS (EI): m/z (%) = 249 (10) [M] + , 219 (15), 163 (59), 149 (23), 120 (35), 106 (100), 91 (29), 77 (25), 65 (14), 51 (14), 43 (59). C 17 H 15 NO (249.31): calcd.…”

Section: -(4-methylbenzyl) Quinoline 1-oxide (3k)mentioning

confidence: 99%

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Visible‐Light‐Promoted Copper‐Catalyzed Regioselective Benzylation of Pyridine N‐Oxides versus Thermal Acylation Reaction with Toluene Derivatives

Kianmehr

Gholamhosseyni

2018

Eur J Org Chem

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Copper‐catalyzed visible light mediated direct C–H bond benzylation of pyridine N‐oxides with toluene derivatives was accomplished by recent developments in photochemical carbon–carbon bond formation through a photo‐induced bond‐dissociation strategy. This visible light driven protocol has been successfully applied to a broad scope of pyridine N‐oxides and toluene derivatives. Furthermore, preliminary research indicates that the acylation reaction can be carried out under thermal reaction conditions. This protocol provides easy access to 2‐benzyl and 2‐acyl pyridine N‐oxide derivatives in the presence of a copper catalyst.

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Section: Resultsmentioning

confidence: 99%

Section: -(4-methylbenzyl) Pyridine 1-oxide (3c)mentioning

confidence: 99%

Section: -(4-methylbenzyl)-4-nitropyridine 1-oxide (3g)mentioning

confidence: 99%

Section: -(4-methylbenzyl) Quinoline 1-oxide (3k)mentioning

confidence: 99%

See 2 more Smart Citations

Visible‐Light‐Promoted Copper‐Catalyzed Regioselective Benzylation of Pyridine N‐Oxides versus Thermal Acylation Reaction with Toluene Derivatives

Kianmehr

Gholamhosseyni

2018

Eur J Org Chem

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“…[2] 2-Acylpyridine N-oxides are used as prochiral ketones in the asymmetric Henry reaction [3] to give tertiary nitro aldols, [4] which are building blocks for the synthesis of pharmaceuticals and agrochemicals [5] (Figure 1, compound A). They show excellent chelating properties in several asymmetric metal-catalysed reactions, [6] and they have also been used as precursors for the synthesis of norbormide (NRB; Figure 1, compound B), which acts as a rat-selective toxicant, [7] vasoconstrictor, and calcium-channel blocker. [8] The direct functionalization of pyridine N-oxides has been investigated, and it has been found to take place with complete selectivity for the 2-position.…”

Section: Introductionmentioning

confidence: 99%