Proceedings
of the III International Conference on the
Chemistry and Biological Activity
of Synthetic and Natural Compounds
CBC2006
Edited by Prof. V.G. Kartsev |
In the opinion of the leading experts both at home and abroad, the series of international conferences on The Chemistry and Biological Activity of Synthetic and Natural Compounds (CBC) has become one of the most important and representative forums on the chemistry and bioactivity of heterocycles held in Russia. The first one, ÑÂÑ-2001, Moscow, was devoted to the chemistry of nitrogen-containing heterocycles and alkaloids; the second conference ÑÂÑ-2003, Moscow, dealt with the chemistry and bioactivity of O,S-containing heterocycles. The major organizers and sponsors of these conferences were InterBioScreen Ltd. and the International Charitable Foundation Scientific Partnership (ICSPF).
The tradition of these scientific forums was carried on by organizing the III International Conference on The Chemistry and Biological Activity of Nitrogen-Containing Heterocycles (CBC-2006) at the Russian Academy of Sciences' Research Center at Chernogolovka. The conference was dedicated to the 90th anniversary of Professor. Alexey Kost's birthday, an outstanding scientist and remarkable educator, Honored Scientist of the Russian Federation. This conference was organized with the participation and support from the Russian Academy of Sciences, Russian Mendeleev Chemical Society, Moscow State University, and Council on Science and Technology under the Moscow Government.
Among invited plenary lecturers are Prof. H.C. van der Plas (University of Wageningen, the Netherlands), Prof. J. Bergman (Novum Unit of Organic Chemistry, Sweden), Prof. M. Mąkosza (Institute of Organic Chemistry, Warsaw, Poland), Prof. L. Fišera (Slovak University of Technology, Bratislava, Slovak Republic), Prof. Atta-ur-Rahman (International Center for Chemical Sciences, University of Karachi, Pakistan), and other noted scientists from Austria, Belgium, France, Germany, Great Britain, Greece, India, Italy, Jordan, the Netherlands, Russia, Sweden, the USA, and the CIS countries (republics of the former Soviet Union).
The words of greetings were received from the Noble Prize laureates Prof. Elias J. Corey (Harvard University, USA) andProf. Jean-Marie Lehn (Institut de Science et d'Ingénierie Supramoléculaires, France).
This two-volume collection presents the full Proceedings of the III International Conference on The Chemistry and Biological Activity of Nitrogen-Containing Heterocycles and containsplenary lectures, oral and poster presentations. These are the original papers submitted by scientists, from both this country and abroad, on the synthesis, chemical transformation, and biological activity of nitrogeneous heterocycles, from simple to complicated condensed systems.
These two volumes are published in Russian and English. To keep with our tradition, vol. 2. is supplemented with the most interesting selected synthetic protocols for the preparation and modification of heterocycles developed in the last few years by chemists in Russia, Ukraine, Belarus, etc. Most of these works were inspired and supported by InterBioScreen.
On behalf of the organizers, I would like to thank all the participants for their contribution to this collection.
Alexey Nikolaevich Kost was my esteemed Teacher. For me, it is of special value that the International Conference ÑÂÑ-2006 has made it possible for scientists from more than 30 countries across the world to get together and pay tribute to this outstanding person, scientist, and edicationalist.
Victor Kartsev,Dr. Sc., Prof.
Chairman, CBC-2006 Organizing Committee
President, Scientific Partnership Foundation
Chairman, Board of directors of InterBioScreen
Plenary lectures |
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Akhrem A.A., Gulyakevich O.V., Mikhal'chuk A.L. [2+4]-Cyclocondensation of monocyclic azomethines with β-di- and β,β'-tricarbonyl compounds in synthesis of azangular heterocycles |
15
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Atta-ur-Rahman, Choudhary M.I. Nitrogen-containing heterocycles from natural sources: Isolation, biological studies, and synthesis |
20
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Bergman J., Stensland B. Cyclization of cyanoethylated ketones as a route to 6-hydroxylated indole derivatives |
28
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Chupakhin O.N., Rusinov V.L., Charushin V.N. Abnormal nucleosides from isosteres of purine |
33
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Elguero J. The structure of pyrazoles in the solid state: Static and dynamic aspects |
41
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Fišera L. Control of regio- and stereoselectivity in nitrone cycloadditions and their utilization in synthesis |
46
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Florio S. o-Lithiation of aziridines and oxiranes as a useful synthetic methodology |
51
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Granik V.G. Biotransformations of heterocyclic nitrogen-containing drugs |
53
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Hajós Gy. Zwitter-ionic heterocycles: A pool of novel polyfused ring systems |
63
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Jordis U. How to use software and integrate databases in the daily practice of heterocyclic chemist |
67
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Kostyanovsky R.G. Nitrogen chirality in heterocyclic chemistry |
72
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Krasnov K.A., Kartsev V.G. Ò-reactions of cyclic b-dicarbonyls in the chemistry of quinoline and isoquinoline systems |
76
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Mąkosza M. Synthesis of indoles via nucleophilic substitution of hydrogen in nitroarenes |
104
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Poroikov V.V., Filimonov D.A., Gloriozova T.A.,
Lagunin A.A. Computer-aided prediction of biological activity for nitrogen-containing organic compounds |
109
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Preobrazhenskaya M.N. Chemistry and biology of ascorbigen |
115
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Sagitullina G.P., Sagitullin R.S. Recyclization of pyridinium salts: New horizons |
121
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Saloutin V.I., Burgart Ya.V., Chupakhin O.N. Design of azaheterocycles based on fluorine-containing 2,4-dioxobutanoates and their derivatives |
129
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Saxena A.K. Substituted arylpiperazines in rational drug design |
135
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Shestopalov A.M., Rodinovskaya L.A., Shestopalov
A.A. Recyclization reactions of degenerate carbo- and heterocycles: Practical retrosynthetic approach to new multicomponent methods for synthesis of N-containing five- and six-membered heterocycles |
146
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Vasilevsky S.F., Balova I.A. New one-pot synthesis and heterocyclization of vic-functionalized aryl(hetaryl)alkadiynes-1,3 |
156
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Oral presentations |
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Abdou W.M., Sediek A.A. Biologically important N-heterocycles and their phosphono derivatives |
163
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Abu-Orabi S.T. 1,3-Dipolar cycloaddition reactions in synthesis of heterocycles |
164
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Adekenov S.Ì. Nitrogen-containing derivatives of natural sesquiterpene lactones |
167
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Agarwal S., Filali S., Fröhner W., Knöll
J., Krahl M.P., Reddy K.R., Knölker H.-J. Application of oxidative cyclizations to the synthesis of bioactive nitrogen-containing heterocycles |
176 |
Akhmetova V.R., Nadyrgulova G.R., Khairullina
R.R., Khafizova S.R., Kunakova R.V., Dzhemilev U.M. One-pot synthesis of novel N,S-containing heterocycles |
187 |
Aripova S.F., Zhalolov I.Zh., Levkovich M.G.,
Tashkhodzhaev B., Khuzhaev V.U., Mirzaev Yu.R. New alkaloids from Arundo donax L. for medicinal applications |
190 |
Atazhanova G.A. N,S-containing terpenoid heterocycles from essential oil of plants |
195
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Bazureau J.P., Legeay J.C., Fraga-Dubreuil J.,
Hakkou H. Ionic liquid-phase technology: A new tool for combinatorial chemistry. Applications in heterocyclic chemistry mediated by microwave dielectric heating |
203
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Beccalli E.M., Broggini G. Pd-Promoted intramolecular formation of C–N bonds in synthesis of heterocyclic systems |
206
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Belous A.R. Endogenous indole compounds: Biological significance of 5-hydroxytryptamine in health and disease—future of drug discovery |
209
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Berestovitskaya V.M., Anisimova N.A., Makarova
N.G. Synthesis of nitrogen-containing heterocycles from b-nitroethenylphosphonates and -carboxylates |
213
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Bölcskei H., Gács-Baitz E., Szántay
Cs. Jr., Kalaus Gy., Szántay Cs. Synthesis of indoloazepines and indoloazocines |
215
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Burgart Ya.V., Pryadeina M.V., Khudina O.G.,
Saloutin V.I., Chupakhin O.N. Synthesis of fluoroalkyl-containing pyrimidines |
219
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Chung M.C. Prodrug design: Improving drug activity |
223
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Danagulyan G.G. Kost–Sagitullin rearrangement with amine exchange and concurrent recyclization of pyrimidinium salts |
228
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Dondoni A., Massi A. Multicomponent syntheses of glycoside-decorated N-heterocyclic pharmacophores |
231
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Drach B.S., Sviripa V.N., Pil'o S.G., Popil'nichenko
S.V., Golovchenko A.V., Brovarets V.S. Functionalized condensed heterocycles from 2-acylamino- 3,3-dichloroacrylonitriles |
236 |
Duburs G., Bisenieks E., Krauze A., Plotniece
A., Sobolevs A., Tirzitis G., Vigante B. Dihydropyridines as biomimetics and bioprotectors |
239 |
Dzvinchuk I.B., Lozinskii M.O. 2-Acylmethyl-1H-benzimidazoles and 2-phenacylbenzothiazole in synthesis of heterocyclic compounds |
243
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Dzvinchuk I.B., Lozinskii M.O. 2-Phenacylbenzothiazole and 2-acylmethyl-1H-benzimidazole hydrazones: Synthesis, structure, cyclization, and recyclization |
249
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Eremkin A.V., Mol'kov S.N., Ershov O.V. Hydrolysis of cyano groups in 2-halo-6-hydroxy-5,5-dialkyl- 5,6-dihydropyridine-3,4,4(1H)-tricarbonitriles |
256
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Ershov A.Yu., Lagoda I.V., Koshmina N.V., Dobrodumov
A.V. Recyclization of isoxazole derivatives |
259
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Fisyuk A.S., Mukanov A.Yu. Domino reactions in synthesis of pyrimido[6,1-a]isoquinolines and pyrimido[6,1-a]-b-carbolines |
262
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Geronikaki A., Incerti M., Zani F., Vicini P. 2-Benzo[d]isothiazolylimino-5-arylidene-4-thiazolidinones: Synthesis and antimicrobial activity |
268
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Gidaspov A.A. bis-Trinitromethylation of 2,4,6-trichloro-1,3,5-triazine |
272
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Gornostaev L.M., Arnold E.V., Beresnev V.A.,
Dolgushina L.V., Lavrikova T.I., Sokolova M.S. Anthraquinone derivatives condensed with pyrrole and triazole rings: Synthesis and properties |
275 |
Gorobets N.Yu., Ermolaev C.A., Dzhavakhishvili
S.G., Sirko S.N., Chernenko V.N., Desenko S.M. 2-Dimethylaminomethylene-1,3-cyclohexanedione derivatives in reaction with methylene-active nitriles |
278 |
Granzhan A., Ihmels H., Viola G. Rearrangements in diazoniapentaphenes and DNA-binding properties of diazoniapolycycles |
282
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Gulyakevich O.V., Mikhal'chuk A.L. Construction of azinone framework by [3+3]-cyclocondensation of b-enaminones with β-ketoesters |
286
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Isak A.D., Pogorelova I.P., Tyupalo N.F., Isak
V.A. Pyrimidine sulfone amides and their derivatives: Synthesis and biological activity |
290
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Kalinin V.N., Shishkov I.V., Moiseev S.K., Shults
E.E., Tolstikov G.A. Synthesis of new dienes and trienes of the morphinan series |
293
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Klochkova I.N., Sazonov A.A. Functionally substituted hydrogenated azines and thiazines: Synthesis and characterization |
296
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Kofanov E.R., Sosnina V.V. Multifunctional heterocyclic compounds from nitriles of aromatic carboxylic acids |
299
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Korotkikh N.I., Raenko G.F., Kiselev À.V., Knishevitsky
À.V., Shvaika Î.P., Glinyanaya N.V., Panov I.S., Cowley À.H., Jones J.N.,
Moore J.A. Stable carbenes. Insertion into Ñ–Í bonds and reaction with ester function. New cleavage and thermal transformation of 1,2,4-triazol-5-ylidenes |
301 |
Kovalenko S.N., Silin À.V., Savchenko Ò.I. Synthesis and reactivity of pyrazolo[4,3-c]quinolines |
305
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Kravchenko A.N., Sigachev A.S., Chikunov I.E.,
Lozhkin B.V., Baranov V.V., Gazieva G.A., Trunova N.S., Lysenko K.A., Belyakov
P.A., Makhova N.N. New horizons in α-ureidoalkylation |
309 |
Kur'yanov V.O., Priskoka U.S., Chupakhina T.A.,
Chirva V.Ya., Katsev A.M., Shishkin O.V., Shishkina S.V., Kotlyar S.A., Kamalov G.L. Heteroaromatic glycosides of neutral and amino saccharides: Synthesis, structure, and biological activity |
312 |
Lesyk R.B., Zimenkovsky B.S., Atamanyuk D.V. Thiopyrano[2,3-d]thiazoles and their derivatives: Synthesis and biological activity |
317
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Levinson F.S., Ermolaeva E.A., Efimov S.I., Evgen'ev
M.I., Varganov R.V., Vasyutina E.A., Shakirova I.M. 4,6-Dichloro-5,7-dinitro- and 4-methoxy-6-chloro-5,7-dinitrobenzo- furazans as new two-position electrophiles |
321 |
Levkovich M.G. Electric charge on atoms and physicochemical properties of alkaloids |
324
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Levkovskaya G.G., Bozhenkov G.V., Savosik V.A.,
Mirskova A.N. Derivatives of 4- and 5-halopyrazoles: Targeted synthesis, structure, and properties |
327
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Likhacheva N.A., Gataullin R.R., Khusnutdinov
R.N., Abdrakhmanov I.B., Tolstikov G.A. Synthesis of 3-methyleneindoles and their analogs from alkenylanilines |
330 |
Makarenko S.V., Berestovitskaya V.M., Sadikov
K.D., Tafeenko V.A., Chernyshev I.V. Potentially bioactive 1,4-benzodiazinones and their heteroanalogs: Synthesis and structure |
335 |
Makhova N.N., Shevtsov A.V., Petukhova V.Yu.,
Kuznetsov V.V., Kislukhin A.A. Transformation of diaziridine ring under the action of ketenes as a new synthetic approach to nitrogen-containing heterocyclic systems |
337 |
Mali A., Shelar M., Shelar A. Antibiotic resistance: A search for new b-lactam antibiotics |
339
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Mamedov V.A., Khafizova E.A. Chelate azolo[a]annelated qunoxalines from phenylhalopyruvates and their structural analogs |
342
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Mareev A.V., Pavlov D.V., Khatashkeev A.V., Medvedeva
A.S., Afonin A.V., Ushakov I.A. Cascade assembling of polyfunctional 1,2-dihydropyridine and related compounds from 3-trimethylsilyl-2-propynal and 2-aminopyridine under microwave activation |
345 |
Medvedeva A.S., Demina M.M., Novokshonov V.V.,
Safronova L.P., Rulev A.Yu., Pavlov D.V., Mareev A.V., Afonin A.V. Synthesis of azidomethyl-1Í-1,2,3-triazoles |
350 |
Mikhalev O.V., Tarasevich B.N., Fedyanin I.V.,
Il'ina I.G. Autocomplexes of nitroaryls with heterocycles: Synthesis and characterization |
355
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Mirzaev Yu.R. Imperialine derivatives: M2-Cholinoblocking activity and perspectives |
357
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Mirzaev Yu.R. Hypotensive ester alkaloids of Veratrum: Problems of clinical implementation |
359
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Mirzaev Yu.R., Kazantseva D.S., Rakhimov Sh.B.,
Vinogradova V.I. New N-benzyl-cytisines: Preliminary pharmacological testing |
364
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Musienko Î.À., Dybenko À.G., Kartsev V.G. Benzo analogs of cuscutamine and canthine |
367
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Nekrasov D.D. N-Cyanation of azaheterocycles and their use as syntonization agents |
371
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Nekrasov D.D., Obukhova A.S. 2-Amino-substituted 6-aryl-1,3-oxazin-4-ones: Synthesis and biological activity |
380
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Nemes A. Synthetic studies on derivatives and metabolites of cis/trans-apovincamine |
383
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Nosova E.V., Lipunova G.N., Laeva A.A., Charushin
V.N. Fluorinated 2-substituted [1,3]benzothiazinones: Synthesis and properties |
389
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Ol'shevskaya V.A., Zaitsev A.V., Savchenko A.N.,
Luzgina V.N., Shtil' A.A., Kalinin V.N. Carboranylporphyrins: Synthesis and bioactivity |
392 |
Paronikyan E.G., Noravyan A.S., Hakobyan Sh.F. New condensed thieno[3,2-d]pyrimidines and thieno[3,2-d]-1,2,3-triazines: Synthesis and bioactivity |
396
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Plaskon' A.S., Ryabukhin S.V., Volochnyuk D.M.,
Tolmachev A.A. 3-Formylchromones in recyclization with 1,3-CCN- and 1,3-ÑÑÑ-binucleophiles |
398
|
Polygalova N.N., Mikhailovskii A.G., Vakhrin
M.I. Carbonyl derivatives of condensed isoquinolines: Synthesis and reactivity |
402
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Popkov S.V., Kovalenko L.V. 1-Azolylmethyl-6-benzylidene-2-alkoxy-2-methyl- and 2,2-dimethylcyclohexanols: Synthesis and bioactivity |
406
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Przheval'skii N.M. Heterohexadiens in synthesis of heterocycles |
410
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Rádl S., Klecán O. New synthetic routes to triptanes |
412
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Samsoniya Sh.A., Trapaidze M.V., Gogrichiani
E.O., Katsadze E.A., Maisuradze J.P., Dzhaparidze K.G. Some spiro derivatives of indole and condensed bis-indoles |
417 |
Semenov V.E., Nikolaev A.E., Giniyatullin R.Kh.,
Lodochnikova O.A., Voloshina A.D., Galiullina L.F., Latypov Sh.K., Reznik
V.S. Pyrimidinophanes with nitrogen atoms in bridging groups: Synthesis and properties |
422 |
Shelyakin V.V., Kartsev V.G., Vorob'ev D.V.,
Lozinskii M.O. Tandem reactions of some metabolites of natural compounds |
425
|
Shestakov A.S., Gusakova N.V., Shikhaliev Kh.S. Cyanamides and their derivatives in reactions of heterocyclyzation |
431
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Shikhaliev Kh.S., Kryl'skii D.V., Falaleev A.V.,
Kovygin Yu.A., Potapov A.Yu. Construction of heterocyclic systems from guanidines and carbonyls |
434 |
Shklyaev Yu.V., Glushkov V.A., Stryapunina O.G.,
Rozhkova Yu.S., El'tsov M.A. Dearomatization of methoxy- and methylarenes as a novel synthetic route to spiro-heterocycles |
436 |
Sirakanyan S.N., Kartsev V.G., Paronikyan E.G.,
Noravyan A.S. Derivatives of 2,7-naphthyridine: Synthesis, transformations, and bioactivity |
446
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Stroganova T.A., Vasilin V.K., Krapivin G.D. Amino acids of the thieno[2,3-b]pyridine series in reactions of intramolecular cyclization |
449
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Suzdalev K.F., Babakova M.N., Den'kina S.V, Kartsev
V.G. Indoles bearing reactive groups for synthesis of combinatorial libraries |
452
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Usova Å.B., Lysenko L.I., Krapivin G.D. 2-Hydroxy-4- and -6-furylacetophenones, furylbenzazines, and azoles: Synthesis and properties |
457
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Van der Eycken E. Microwave irradiation: A 'green tool' in 2(1H)-pyrazinone chemistry |
460
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Veinberg G., Vorona M., Shestakova I., Kanepe
I., Lukevics E. Antitumor compounds from 3-alkylidene-2-azetidinone as a template |
464
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Velikorodov À.V. Quinones and quinoids in synthesis and modification of indoles |
466
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Vizer S.A., Dedeshko E.H., Erzhanov K.B., Dembitskii
V.M. Synthesis of N-containing heterocycles from a-propargyl- b-dicarbonyls and their O-phosphoryl derivatives |
469
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Volochnyuk D.M., Pushechnikov A.O., Pinchuk A.M.,
Tolmachev A.A. Fused 1,5,2-diaza- and 1,5,2-oxazaphosphinines: Synthesis and properties |
474
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Voskressensky L.G., Vorob'ev I.V., Varlamov A.V. Unusual reactions of tetrahydrobenzo[b][1,6]naphthyridines with activated alkynes |
480
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Zobov V.V., Semenov V.E., Kataev V.E., Akamsin
V.D., Reznik V.S. Tetraalkylammonium derivatives of uracil and their macrocyclic analogs as potential neuromuscular transmission modulators |
482
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Author index |
485–488
|
Poster presentations |
5-288
|
Selected synthetic protocols |
289-412
|
Author index |
413-420
|