Alexey V. Tkachev

SYNTHESIS OF 2-ALKYL AND 2-ARYL PYRIMIDINES FROM β-CHLOROVINYL KETONES OF CYCLOPENTANONE TYPE

Amidines react in the presence of NaHCO3 with β-chlorovinyl ketones, prepared regioselectively by the reaction of 2-acetylcyclo- pentanone-type diketones with PPh3-CCl4 in 73–78% yield, to afford 2-alkyl (aryl)-pyrimidines annelated with cyclopentane derivatives in 79–87% yields.

Study of chiral β-enaminones prepared from pyrrolidine, cytisine, salsoline and 2-amino-1-(4-nitrophenyl)propane-1,3-diol: resolution of salsoline via diastereomeric modified carane-type β-enaminones

Abstract A series of novel optically active β-enaminones have been prepared regio- and stereoselectively from primary and secondary amines (pyrrolidine, cytisine salsoline and 2-amino-1-(4-nitrophenyl)propane-1,3-diol) and (+)-3-carene-derived β-chlorovinylketone. Resolution of the isoquinoline alkaloid salsoline has been demonstrated as well as isolation of a single diastereomeric adduct from racemic 2-amino-1-(4-nitrophenyl)propane-1,3-diol.

Volatile Oil-Bearing Flora of Siberia VIII: Essential Oil Composition and Antimicrobial Activity of Wild Solidago virgaurea L. from the Russian Altai

Abstract Distillation of the fresh flowering tops of wild-growing Solidago virgaurea L. collected from the Russian Altai at 290 m and 650 m yielded 0.22% and 0.07% pure light yellow oil, respectively. GC and GC/MS analyses of the oils revealed that the main components from 290 m were α-pinene (36.5%), myrcene (14.8%), β-caryophyllene (10.5%), germacrene D (8.2%), β-pinene (7.1%) and limonene+β-phellandrene (6.4%). The oil from the sample collected at 650 m had benzyl benzoate (57.0%), β-caryophyllene (6.3%), germacrene D (6.0%), α-pinene (4.4%) and α-humulene (4.0%) as major components, suggesting polymorphism or the existence of different chemoytpes. Using the disc diffusion method we tested the activity of the oil obtained from 290 m against five microbes of health and environmental importance. It showed complete inhibition or killed Aspergillus niger and Staphylococcus aureus, strong inhibition of Saccharomyces cervisiae, and low activity against Escherichia coli, but no effect on Pseudomonas aeruginosa.

Chemical screening of essential oil bearing flora of Siberia. IV. Composition of the essential oil of Nepeta sibirica L. tops from Altai Region

Abstract Distillation of fresh fowering tops of Nepeta sibirica L., yielded 1.0% light yellow mobile oil. GC and GC/MS analysis of the oil composition revealed that the major components were neoepinepetalactone (78.8%) and germacrene D (9.4%), representing 88.2% of the total oil.

Chemical Screening of Essential Oil Bearing Flora of Siberia V. Composition of the Essential Oil of Chaerophyllum prescottii DC Tops from Altai Region

Abstract Distillation of the fresh fowering tops of Chaerophyllum prescottii DC collected from Altai region of Siberia yielded 0.22% mobile colorless oil. Analysis of the oil by GC, GC/MS for the frst time has revealed the presence of 18 substances with the major components consisting of (E)-β-ocimene (35.6%), (Z)-β-ocimene (19.4%), γ-terpinene (18.8%), myrcene (10.6%) and terpinolene (4.6%), representing 89.0% of the total oil, while 11.0% of the oil comprised other minor components.

Novel optically active pyrazole ligands derived from (+)-3-carene

Abstract Reactions of chiral β-diketone with racemic hydrazines as well as reaction of chiral pyrazole with cyclohexene epoxide and trans-stilbene epoxide have been examined as the routes to optically active pyrazolylethanols. Diastereomerically pure products have been isolated by crystallization or column chromatography in good yields.

Chemical Screening of Volatile Oil-Bearing Flora of Siberia VIII.: Variations in Chemical Composition of the Essential Oil of Wild Growing Seseli buchtormense (Fisch. ex Sprengel) W. Koch from Different Altitudes of Altai Region

Abstract Distillation of the flowering tops of Seseli buchtormense (Fisch. ex Sprengel) W. Koch obtained from various altitudes of Altai Region yielded 0.21% (300 m.a.s.l.), 32% (400 m.a.s.l.), 30% (700 m.a.s.l.) and 0.40% (2030 m.a.s.l.), of aromatic pure mobile oil. Analysis of the oil samples using GC, GC/MS gave 82 components. The major components were sabinene (17.7–25.1%), α-pinene (5.3–14.6%), (E)-nerolidole (5.5–11.6%), β-phelandrene (2.5–7.0%), β-myrcene (3.3–6.6%), δ-kadinene (3.0–6.0%), germacrene D-4-ol (3.1–4.6%), α-bosabolol (0.0–7.7%), fenchone (0.5–7.0%) and limonene (0.8–4.5%).

Chemical Screening of Volatile Oil-bearing Flora of Siberia IX. Variations in Chemical Composition of the Essential Oil of Heteropappus altaicus Willd. (Novopokr.) Growing Wild at Different Altitudes of Altai Region, Russia

Abstract Distillation of the fresh flowering tops of Heteropappus altaicus Willd. (Novopokr.) collected from four different altitudes of Altai Region of Siberia yielded mobile, dark green to yellowish oils, depending on the altitude and location of collection. GC and GC/MS analyses of the oils revealed 42 components, of which 65–91% were monoterpenoids and 7–31% were sesquiterpenoid. The oil obtained from 330 m had α-pinene (18.6%), myrcene (18.6%), β-phellandrene (17.2%), (E)-β-ocimene (12.9%) and germacrene D (11.9%), while samples from 600 m consisted of myrcene (26.4%), α-pinene (23.2%), β-phellandrene (18.0%), (E)-β-ocimene (9.9%), germacrene D (4.3%) and sabinene (4.2%). The oil from 120 m had -pinene (22.0%), β-phellandrene (21.6%), myrcene (19.5%), trans-β-ocimene (11.3%), germacrene D (7.2%) and limonene (4.5%) as major components. At 1550 m the major components were germacrene D (22.0%), myrcene (18.0%), β-phellandrene (14.0%), α-pinene (11.3%) and (E)-β-ocimene (9.2%).

Chemical Screening of Essential Oil Bearing Flora of Siberia II. Composition of the Essential Oil of Schizonepeta annua (Pallas) Schischkin Leaves from Altai Region

Abstract The chemical composition of the leaf oil of Schizonepeta annua (Pallas, Schischkin) from Altai Region, Siberia, which was obtained in 4.0% yield, was investigated by GC and GC/MS. The major components were thymol (48.1%), γ-tepinene (18.1%), carvacrol (9.6 %) and p-cymene (9.0%).

Chemical Screening of Essential Oil Bearing Flora of Siberia I. Composition of the Essential Oil of Galatella biflora (L.) Nees Vegetative Tops From the Altai Region

Abstract An essential oil sample obtained from the vegetative tops of Galatella biflora (L.) Nees was analyzed by GC and GC/MS. A light blue mobile oil (1.44%) was obtained. The major components were α-pinene (34.7%), (E)-β-ocimene (15.0%), β-pinene (9.9%), myrcene (7.4%) and limonene (6.2%).