Pyridine glutarimides

The product is a yellow solid that is air sensitive. It decomposes at 210 °C without melting. It is soluble in hot toluene but the solubility is low. It is insoluble in THF, diethyl ether, acetone, CH2C12, pyridine, and methanol. The IR spectrum (KBr disk) contains a strong, sharp peak at 1560cm-1. The product reacts with carbon monoxide affording glutarimide in a 66% yield and Ni(CO)3(tcyp). 

A need for a synthetic entry toward simple and structurally complex alkaloids prompted development of methodology to prepare a variety of azabicyclo[n.3.1] alkenes in good yields utilizing protected 2,6-cA-diaIkenyl piperidines, prepared from glutarimide or 4-methoxy pyridine and catalyzed by (2a) and (4a) (equation 1)." " ... 

N(2-Indolylethyl)glutarimide, 871 Inosine, 740-741 N-oxide, 754 Inositol, 179 -2-carboxylic acid, 326 derivatives, 740 hexamethyl ether, 683 Inositols, 256 Iodic acid, 496 Iodine, 495-500,1107, 1281 Iodine azide, 500-501 Iodine isocyanate, 501 Iodine monobromide, 501-502 Iodine monochloride, 258, 502 Iodine-Morpholine complex, 502-SOS Iodine pentafluoride, 503 Iodine-Pyridine, 503-504 Iodine-Silver salts, 504 lodoacetamide, 504-505 lodoacetone, 1188... 

Fig. 6 Chromatograms of extractions from virgin and recycled polyamide 6.6 after 25 h of thermo-oxidation at 100 °C. Identity of the peaks is 1 = cyclopentanone, 2 = 2-methylpyridine, 3 = pentanoic acid, 4 = butanamide, 5 = 2-ethylcyclopentanone, 6 = 2,4,6-trimethylpyridine, 7 = pentanamide, 8 = 3-(l-methylethyl)pyridine, 9 = 2-butylpyridine, 10 = N,N-hexamethylenebisformamide, 11 = 2-butylcyclopentanone, 12 = glutarimide, 13 = l-propyl-2,5-pyrrolidinedione, 14 = 2-pentylcyclopentanone, 15 = caprolactam, 16 = azepane-2,7-dione, 17 = 2-cyclopentyl-cyclopentanone, 18= l-butyl-2,5-pyrrolidinedione, 19 = l-pentyl-2,5-pyrrolidinedione, 20 = 2-butyl-3,5-dimethylethylpyridine, L1-L7 = linear C13-C17 alkanes and alkenes from lubricant, = silicone from septa used to seal vials. Reprinted from [65] with permission of John WUey Sons, Inc. John Wiley Sons, Inc (2002)...

This facile synthesis of halopyridines could be extended to a-methyl- and o,a -dimethylglutarimide ( ). The reaction of glutarimide with phosphorus pentabromide proceeds similarly to afford a mixture of 2,3,6-tribromo-pyridine and 2,3,5,6-tetrabromopyridine ( ). 

The insecticide chlorpyrifos, developed by Dow, is mainly produced not from pyridine, but by reaction of glutarimide and PCI5 followed by nucleophilic chlorine exchange, via 3,5,6-trichloropyrid-2-one. 

Partial hydrolysis-cyclization of di[ C]nitriles in contrast produces dilabeled amine heterocycles. [2,6- C2]Glutarimides are the most common products because of their utility as intermediates to pyridines they have been prepared by several different methods in yields of up to... 

Figure 7.14 Preparation of carbon-14-labeled pyridine derivatives from [2,6- " C]glutarimide...

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