3- Pyridyl ethyl ketone

Quin, L.D. 3-Pyridyl methyl ketone and 3-pyridyl ethyl ketone as constituents of hurley tobacco cigarette smoke Southeastern Regional Am. Chem. Soc. Mtg., Richmond, VA (1959). 

Scholler, R. 3-Pyridylathylketon im Tabakrauch [3-Pyridyl ethyl ketone in tobacco smoke] Fachhche Mitt. Osterr. Tabakregie 1935(3) 7. 

Both cigar and cigarette smoke contain a base which can be extracted with ether from an acid solution (pH 3.0-3.5) (454). It proved to be identical with 3-pyridyl ethyl ketone (CLXXXVII) already synthesized by Engler (455). 

Reactions of 3- and 4-piperidone-derived enamines with a dienester gave intermediates which could be dehydrogenated to tetrahydroquinolines and tetrahydroisoquinolines (678). The methyl vinyl ketone annelation of pyrrolines was extended to an erythrinan synthesis (679). Perhydrophenan-threnones were obtained from 1-acetylcyclohexene and pyrrolidinocyclo-hexene (680) or alternatively from Birch reduction and cyclization of a 2-pyridyl ethyl ketone intermediate, which was formed by alkylation of an enamine with a 2-vinylpyridine (681). 

DIMETHYLAMINOPHENYL-2-((4-PHENYL-l,2,5.6-TETRAHYDRO-l-PYRIDYL)ETHYL) KETONE see DPS700... 

Glycerol Pyridyl ethyl ketone Components Phytosterol ( )... 

Propanone, 1-(3-pyridinyl)- pyridyl ethyl ketone 111-13, XVII.B-2 ... 

In one case, the intermolecular Heck reaction of 3-pyridyltriflate with ethyl acrylate was accelerated by LiCl to give 159 [127,128], Here, both electronic and steric effects all favored p-substitution. In another case, however, electronic effects prevailed and complete a-substitution was observed. In the presence of an electron-donating substituent (i.e., a protected amine), 3-bromopyridine 160 was coupled with f-butoxyethylene to give 3-pyridyl methyl ketone 162 [126]. The regiochemistry of the Heck reaction was governed by inductive effects, leading to intermediate 161. 

Dicyclohexyl-2-(2 -pyridyl)ethylene hydrochloride (15 grams) in 150 ml of ethanol was hydrogenated in the presence of platinum oxide at about 60 pounds per square inch of hydrogen pressure. The product, 1,1-dicyclohexyl-2-(2 -piperidyl)ethane hydrochloride, crystallized from a mixture of methanol and methyl ethyl ketone as a white solid melting at 243° to 245.5°C. 

SYNS KETONE, 4-PHENYL-l-PIPERAZINYLMETHYL-3-PYRIDYL- l-(2-KETO-2-(3 -PYRIDYL)ETHYL)-4-(PHENYL)PIPERAZINE... 

Kl=acetophenone,K2=n-propyl pyruvate (CPl3C0C02-n-Pr),K3=i-butyl levulinate (CH3COCH2CH2C02- -Bu),K4=f-BuCOCH3,K5=3-MeOPhCOCH3,K6=2-py-ridyl methyl ketone, K7=l-tetralone, K8=l-acetylnaphthalene,K9=2-acetylnaphthalene,K10=ethyl levulinate,Kll=2-octanone,K12=2-phenylcyclohexanone, K13=3-pyridyl methyl ketone, K14=Me2HSiOCH2COCH3,K15=Me2HSiOCH2COPh,K16=l-cyclohexenyl methyl ketone, K17=ethyl pyruvate, K18=2,2-dimethyl-acetylacetonate,K19=methyl levulinate, K20=3,3-dimethyl-pentane-2,4-dione, K21=2-nonanone,K22=PhCOCH2Cl. 

Other reagents are available for introducing the 2-oxo group. Thus, 2-amino-3-pyridyl phenyl ketone, ethyl carbamate, and zinc chloride, fused for 45 min at 230°C, gave a good yield of 4-phenylpyrido[2,3-d ] pyrimidin-2-one (see 3). In addition, 2-ferf-butylamino-3-pyridylphenylketonimine, phosgene, and triethylamine, stirred in cold benzene for 10 min, produced... 

Ethyl-2-pyridyl methyl ketone, SCI. l- 4-Ethyl-2-pyridinyI)... 

Craig s synthesis of nicotine (V to VII, p. 42) proceeds via nomicotine. Nicotinic acid nitrile reacts with the Grignard reagent derived from ethyl y-bromopropyl ether to give 3-pyridyl-y-ethoxypropyl ketone (V). This yields an oily oxime (VI) reducible to a-(3-pyridyl)-a-amino-8-ethoxy-w-butane (VII), which with 48 per cent, hydrobromic acid at 130-3° gives womicotine, and this on methylation yields dZ-nicotine. 

---