The Reaction of Oxalyl Chloride with Amides. IV. Synthesis of Acyl Isocyanates

Speziale, A. J.; Smith, Lowell R.; Fedder, Joan E.

doi:10.1021/jo01023a501

Cited by 65 publications

(17 citation statements)

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“…Also, carboxylic acids with sensitive functional groups such as alkyl, ether, amide and ester wherein the previously described protocols would not work, can be converted efficiently to corresponding acyl isothiocyanates (Table 2, entries 8,9,10,11,12,18,19,20).…”

Section: Resultsmentioning

confidence: 99%

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Direct and Facile Synthesis of Acyl Isothiocyanates from Carboxylic Acids Using Trichloroisocyanuric Acid/Triphenylphosphine System

Entezari¹,

Akhlaghinia²,

Rouhi-Saadabad³

2014

Croat. Chem. Acta

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Section: Resultsmentioning

confidence: 99%

“…[4][5][6][7][8][9][10][11][12][13][14] which are mainly based on the reaction of acyl halides with thiocyanate ion. 2,6 Acyl halides are not always easy to access or store.…”

Section: Introductionmentioning

confidence: 99%

Direct and Facile Synthesis of Acyl Isothiocyanates from Carboxylic Acids Using Trichloroisocyanuric Acid/Triphenylphosphine System

Entezari¹,

Akhlaghinia²,

Rouhi-Saadabad³

2014

Croat. Chem. Acta

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“…Preparation of acyl-isocyanates was adapted from literature [23]: Oxalylchloride (1.1 equivalent) was added to a suspension of 3,5-dimethyl-benzamide 2 [24] (200 mg, 1.341 mmol) in anhydrous 1,2-dichloroethane (15 mL) and the mixture was heated at reflux temperature for 1 day. The volatiles were distilled off under diminished pressure and toluene (2 × 5 mL) was evaporated from the residue to remove the rest of oxalylchloride.…”

Section: Methodsmentioning

confidence: 99%

Glycogen Phosphorylase Inhibitor N-(3,5-Dimethyl-Benzoyl)-N’-(β-D-Glucopyranosyl)Urea Improves Glucose Tolerance under Normoglycemic and Diabetic Conditions and Rearranges Hepatic Metabolism

et al. 2013

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Glycogen phosphorylase (GP) catalyzes the breakdown of glycogen and largely contributes to hepatic glucose production making GP inhibition an attractive target to modulate glucose levels in diabetes. Hereby we present the metabolic effects of a novel, potent, glucose-based GP inhibitor (KB228) tested in vitro and in vivo under normoglycemic and diabetic conditions. KB228 administration enhanced glucose sensitivity in chow-fed and obese, diabetic mice that was a result of higher hepatic glucose uptake. Besides improved glucose sensitivity, we have observed further unexpected metabolic rearrangements. KB228 administration increased oxygen consumption that was probably due to the overexpression of uncoupling protein-2 (UCP2) that was observed in animal and cellular models. Furthermore, KB228 treatment induced mammalian target of rapamycin complex 2 (mTORC2) in mice. Our data demonstrate that glucose based GP inhibitors are capable of reducing glucose levels in mice under normo and hyperglycemic conditions. Moreover, these GP inhibitors induce accommodation in addition to GP inhibition - such as enhanced mitochondrial oxidation and mTORC2 signaling – to cope with the glucose influx and increased glycogen deposition in the cells, however the molecular mechanism of accommodation is unexplored.

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“…chloride or phosgene into the corresponding isocyanates, the analogous reaction with ureas has not previously been recorded. We have now prepared isocyanates of type ( 3 ) (water-clear distillable liquids) by a simple method, namely addition of N-chlorocarbonyl isocyanate [2)[41 to Schiff bases ( I ) .…”

Section: 8-dimethylbenzopteridinementioning

confidence: 99%