N-p-Cyanoethylation

A 2.42 g (0.01 mole) of ethyl N-(p-cyanoethyl)indole-2-carboxylate is suspended in acetic anhydride (20 ml). The suspended compound is hydrogenated on a Parr shaker in the presence of Raney nickel. The uptake of hydrogen is complete after 1.5 h. The product recovered is recrystallized from benzene-hexane. The product obtained is ethyl l-(3-acetamidopropyl)indole-2-carboxylate, melting point 83.5°-84.5°C. 

Synonyms 2-(N-(2-Cyanoethyl)-N-cyclohexyl) aminoethanol N-(P-Cyanoethyl)-N-(P-hydroxyethyl) aniline Cyclohexylcyanoethylethanolamine... 

N-2-Cyanoethylaneline, 36, 6 N-2-Cyanoethyl-p-anisidine, 36, 7 Cyanoethylation, of aniline, 36, 6 of o-chloroaniline, 38, 14 of ethyl phenylcyanoacetate, 30, 80 N-2-Cyanoethyl- -chloroaniline,... 

The 3 -aminoacylated dinucleotides 66 have been prepared by reaction of N-FMOC amino acid fluorides with the p-cyanoethyl-protected dinucleotide. Deprotection with oximate removes all protecting groups without disturbing the aminoacyl linkage. ... 

N -(2-Cyanoethyl)-L-glutamine was isolated from seeds of Lathyrus odoratus 203), The structure was established by elemental analysis, acid hydrolysis with the subsequent isolation of L-glutamic acid and P-alanine and by synthesis. The y-linkage was inferred from the acid lability 299),... 

N -(2-Cyanoethyl)-L-glutamine was originally isolated from seeds of Lathyrus odoratus as the agent causing lathyrism in rats (299). y-L-Glutamyl-P-cyano-L-alanine was likewise isolated from seeds of Vida saliva and showed to be responsible for the toxicity of these seeds to-... 

Diastereomers of deoxynucleoside 3 -(0-P-cyanoethyl, N-diisopropyl)-phosphoramidites can be separated by chromatography. The proton n.m.r. spectra show characteristic differences which can be used to assign absolute configurations at phosphorus.a study has been reported on the use of such intermediates for oligoribonucleotide synthesis. 1 4... 

A soln. of p-nitro-N,N-bis-(2-cyanoethyl)benzamide in abs. ethanol treated at reflux with a soln. of Na in abs. ethanol, refluxing continued for 2-5 hrs. p-nitro-N-(2-cyanoethyl)benzamide. Y 87%. F. e., also with simultaneous hydrolysis and reduction, and use of KOH/alcohol as catalyst, s. L. A. Pursglove, J. Org. Chem. 24, 576 (1959). 

Zon, G., Gallo, K. A., Samson, C. J., Shao, K., Summers, M. F., and Byrd, R A. (1985) Analytical studies of mixed sequence oligodeoxyribonucleotides synthesized by competitive coupling of either methyl- or P-cyanoethyl-N,A -diisopropylamino phosphoramidite reagents, including 2 -deoxyinosine Nucl Acids Res. 13,8181-8196. 

Sinha, N. D, Biernat, J., McManus, J., and Koster, H (1984) Polymer support oligonucleotide synthesis XVIII, use of P-cyanoethyl-lV,V-dialkyl-amino-W-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product Nucl Acids Res 12,4539-4557. 

Alkylation at the ind-N of l,2,3,4-tetrahydro-j8-carbolines has been carried out with alkyl halide after treatment with sodamide in the usual manner. Cyanoethylation of a p /r-V-substituted tetrahydro-jS-carboline in the presence of Triton B yields the corresponding 9-cyanoethyl derivative. Similarly, treatment of p / -V-methyl-l,2,3,4,4a,9b-hexahydro-y-carboline with sodamide, followed by benzyl chloride, leads to the ind-A -benzyl-substituted derivatives. l-Oxo-l,2,3,4-tetrahydro-j8-carboline yields the ind-A -methyl derivative directly with dimethyl sulfate.Prolonged treatment with sodium hydride, followed by methyl iodide, yields the 2,9-dimethyl derivative. Heating with sodium hydride in acetone followed by the addition of dimethyl sulfate gives rise to the ind-V-methyl derivative. ... 

Octahydroazocine (1) behaves as a typical secondary amine and forms an azeotrope with water, b.p. 96 °C (52M386). It can be transformed into 1-nitroso and 1-amino derivatives in the usual way (74JMC948). The imine (1) can also be cyanoethylated, and adds ethylene oxide (59MI51900) to give the N- hydroxyethyl derivative. Attempts to convert (1) to an enamine by oxidation with silver acetate gave only a low yield of pyridine (52M386). 

A novel route to the 4,7-phenanthroline ring system involves cyclization of N,N,N N -tetrakis-2 -cyanoethyl-p-phenylenediamine... 

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