S 98 Synthesis of 8-R-9c-alkyl-1-aryl-2-benzyl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-aza-cyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones and reaction thereof with acetic anhydride [Text] / V. V. Shchepin, P. S. Silaichev, A. R. Racitin, M. I. Kodess // Tetrahedron Letters. - 2006. - Vol. 47, № 4. - P557-560 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reaction of zinc enolates synthesized from 1-aryl-2,2-dibromoalkanones and zinc with 6-R-2-oxochromene-3-carboxylic acid N-benzylamide affords 8-R-9c-alkyl-1-aryl-2-benzyl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-aza-cyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones. Acylation of these compounds is accompanied by an unexpected rearrangement producing a sole geometrical isomer of 4?-alkyl-5?-aryl-1?-benzyl-3,4,2?,3?-tetrahydro-2,2?-dioxospiro[chroman-3,3?-pyrrol]-4-yl acetates \\\\Expert2\\nbo\\Tetrahedron Letters\\2006, v. 47, p.557.pdf |
R 30 Reactions of zinc enolates derived from 1-aryl-2,2-di-bromoalkanones with 2-acyl-3H-benzo[f]chromen-3-ones, 6-bromo-2-oxochromene-3-carboxamides, and 3-oxo-3H-benzo-[f]chromene-2-carboxamides [Electronic resource] / V. V. Shchepin, M. M. Kalyuzhnyi, P. S. Silaichev, M. A. Ezhikova, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2004. - Vol. 40, № 9. - P1353-1358 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Zinc enolates derived from substituted 1-aryl-2,2-dibromoalkanones reacted with 2-acyl-3H-benzo-[f]chromen-3-ones to give 1-alkyl-1-aroyl-1a-acyl-1a, 9c-dihydro-1H-3-oxacyclopropa[c]phenanthren-2-ones which were formed as a single stereoisomer. Reactions of the same zinc enolates with 6-bromo-2-oxo-chromene-3-carboxamides (piperidides and morpholides) afforded 1-aroyl-6-bromo-1-alkyl-1a-piperidino-(morpholino)carbonyl-1a,7b-dihydrocyclopropa[c]chromen-2-ones with high stereoselectivity. Likewise, 1-benzoyl-1-methyl-1a-morpholinocarbonyl-1a, 9c-dihydro-1H-3-oxacyclopropa[c]phenanthren-2-one was obtained by reac-tion with 3-oxo-3H-benzo[f]chromene-2-carboxylic acid morpholide \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2004, 40 (9), 1353.pdf |
R 30 Reaction of organozinc reagents formed in reaction of dibromomalonic acid dialkyl esters and zinc, with 2-arylmethylenemalonic acid dinitriles and 3-aryl-2-cyanopropenoic acid methyl esters [Electronic resource] / V. V. Shchepin, Yu. G. Stepanyan, P. S. Silaichev, M. I. Kodess // Russian Journal of General Chemistry. - 2006. - Vol. 76, № 12. - P1919-1921 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Organozinc compounds, obtained from dibromomalonic acid dialkyl esters and zinc, react with 2-arylmethylmalonic acid dinitriles and 3-aryl-2-cyanopropenoic acid methyl esters forming 3-aryl-2,2-dicyanocyclopropane-1,1-dicarboxylic acid dialkyl esters and 3-aryl-2-cyanocyclopropane-1,1,2-tricarboxylic acid trimethyl esters \\\\Expert2\\nbo\\Russian Journal of General Chemistry\\2006, V. 76, N 12, p.1919.pdf |
R 30 Reactions of zinc enolates derived from 1-aryl-2-bromo-2-phenylethanone and 2-bromoindan-1-one with alkyl 2-oxochromene-and 6-bromo-2-oxochromene-3-carboxylates [Electronic resource] / V. V. Shchepin, A. E. Korzun, M. I. Vakhrin, P. S. Silaichev, M. A. Ezhikova, M. I. Kodess // Russian Journal of General Chemistry. - 2006. - Vol. 76, № 5. - P777-780 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Zinc enolates derived from 1-aryl-2-bromo-2-phenylethanone react with alkyl 2-oxochromene-3-carboxylates and methyl 6-bromo-2-oxochromene-3-carboxylate to give, respectively, alkyl 4-(2-aryl-2-oxo-1-phenylethyl)-2-oxochroman-3-carboxylates and methyl 6-bromo-4-(2-aryl-2-oxo-1-phenylethyl)-2-oxochroman-3-carboxylate as a single stereoisomer. Zinc enolates derived from 2-bromoindan-1-one react with alkyl 2-oxochromene-3-carboxylates to give alkyl 2-oxo-4-(1-oxoindan-2-yl)chroman-3-carboxylates as a single stereoisomer \\\\Expert2\\nbo\\Russian Journal of General Chemistry\\2006, V. 76, N 5, p.777.pdf |
C 98 Cyclopropanation of N-Substituted 2-Oxochromene- and 6-Bromo-2-oxochromene-3-carboxamides with Zinc Enolates Derived from 1-Aryl-2,2-dibromoalkanones [Electronic resource] / V. V. Shchepin, P. S. Silaichev, R. V. Shchepin, M. A. Ezhikova, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 4. - P527-534 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Zinc enolates derived from 1-aryl-2,2-dibromoalkanones react with N-cyclohexyl-2-oxochromene-3-carboxamides to give N-cyclohexyl-1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides mainly as cis isomers with respect to the substituents in positions 1 and 1a. Reactions of the same zinc enolates with N-benzyl-2-oxochromene-3-carboxamide and N-benzyl-6-bromo-2-oxochromene-3-carboxamide lead to formation of 1-aryl-2-benzyl- and 1-aryl-2-benzyl-6-bromo-1-hydroxy-9c-alkyl-1,2,9b,9c-tetrahydro-5-oxa-2-azacyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones. The reaction of zinc enolates with N-aryl-2-oxochromene-3-carboxamides in a weakly polar solvent (diethyl ether or ethyl acetate) affords mixtures of cis-N-aryl-1-aroyl-1-alkyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides and their cyclic isomers, 9c-alkyl-1,2-diaryl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-azacyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones, the latter prevailing. N-Substituted 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides in which the aroyl group on C1 and the carboxamide group on C1a are arranged trans are formed by reactions of zinc enolates with the corresponding 2-oxochromene-3-carboxamides in the presence of hexamethylphosphoric triamide \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2005, 41 (4), 527.pdf |
S 53 Shchepin, V. V. Reaction of zinc enolates prepared from 2,2-dibromoindan-1-one or 2,2-dibromo-1-tetralone and zinc with 2-oxochromen-3-carboxylic acid derivatives [Electronic resource] / V. V. Shchepin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2007. - Vol. 43, № 10. - P1441-1445 Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2007, 43 (10), 1441.pdf |
C 98 Cyclopropanation of 2-arylmethylidenemalononitriles, alkyl 3-aryl-2-cyanoprop-2-enoates, and N-substituted 3-aryl-2-cyanoprop-2-enamides with bromine-containing zinc enolates [Electronic resource] / V. V. Shchepin, Yu. G. Stepanyan, P. S. Silaichev, M. A. Ezhikova, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2007. - Vol. 43, № 7. - P1002-1007 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Zinc enolates derived from 2,2-dibromoindan-1-one and 2,2-dibromo-1,2,3,4-tetrahydronaphthalen-1-one reacted with 2-arylmethylidenemalononitriles, alkyl 3-aryl-2-cyanoprop-2-enoates, and N-substituted 3-aryl-2-cyanoprop-2-enamides to give, respectively, 3-aryl-1?-oxo-1?,3?-dihydrospiro[cyclopropane-1,2?-indene]-2-2-dicarbonitriles, 3-aryl-1?-oxo-3?,4?-dihydro-1?H-spiro[cyclopropane-1,2?-naphthalene]-2,2-dicarbonitriles, alkyl 3-aryl-2-cyano-1?-oxo-1?,3?-dihydrospiro[cyclopropane-1,2?-indene]-2-carboxylates, alkyl 3-aryl-2-cyano-1?-oxo-3?,4?-dihydro-1?H-spiro[cyclopropane-1,2?-naphthalene]-2-carboxylates, and N-substituted 3-aryl-2-cyanol-1?-oxo-3?,4?-dihydro-1?H-spiro[cyclopropane-1,2?-naphthalene]-2-carboxamides as a single diastereoisomer. The stereoconfiguration of the products was determined by 1H and 13C NMR spectroscopy \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2007, 43 (7), 1002.pdf |
R 30 Reaction of organozinc reagents prepared from bromomalonic acid esters and zinc with 3-aryl-2-cyanopropenoic acid primary amides [Electronic resource] / V. V. Shchepin, P. S. Silaichev, Yu. G. Stepanyan, N. Yu. Russkikh, M. I. Vakhrin, M. A. Ezhikova, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 11. - P1625-1629 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Organozinc compounds prepared from bromomalonic acid esters and zinc react with 3-aryl-2-cyanopropenoic acid primary amides giving a single diastereomer of the corresponding 1-R?-4-aryl-2,6-dioxo-5-cyanopiperidine-3-carboxylic acid esters, or 3-R?-6-aryl-2,4-dioxo-5-cyano-3-azabicyclo[3.1.0]hexene-1-carboxylic acid esters \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (11), 1625.pdf |
R 30 Reactions of zinc enolates derived from 1-aryl-2-bromo-alkanones and 1-aryl-2-bromo-2-phenylethanone with 3-aroyl-6-bromochromen-2-ones and 2-benzoylbenzo[f]chromen-3-one [Electronic resource] / V. V. Shchepin, A. E. Korzun, M. I. Vakhrin, P. S. Silaichev, M. A. Ezhikova, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 9. - P1344-1347 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 3-Aroyl-6-bromochromen-2-ones and 2-benzoylbenzo[f]chromen-3-one reacted with zinc enolates derived from 1-aryl-2-bromoalkanones and 1-aryl-2-bromo-2-phenylethanone to give, respectively, 4-(1-alkyl-2-aryl-2-oxoethyl)-3-aroyl-6-bromochroman-2-ones and 1-(2-aroyl-1-methyl-2-oxoethyl)-2-benzoyl-1,2-dihydrobenzo[f]chromen-3-ones as a single stereoisomer. Treatment with acetic anhydride of the intermediate product obtained from 3-benzoyl-6-bromochromen-2-one and [1-(4-chlorophenyl)-2-phenylethen-1-yloxy]-zinc(II) bromide resulted in the formation of 3-(1-acetoxy-1-phenylmethylidene)-6-bromo-4-[2-(4-chlorophenyl)-2-oxo-1-phenylethyl]chroman-2-one \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (9), 1344.pdf |
R 30 Reaction of N-substituted 2-oxochromen-3-carboxamides with bromoderivatives of zinc enolates prepared from alkyl 2,2-dialkyl-4,4-dibromo-3-oxoalkanoates and zinc [Electronic resource] / V. V. Shchepin, P. S. Silaichev, N. Yu. Russkikh, M. I. Vahrin, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 8. - P1157-1163 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ZINC ENOLATES -- CARBOXAMIDES -- E-POSITION Аннотация: Zinc enolates obtained from ethyl 2,2-dialkyl-4,4-dibromo-3-oxobutanoates and zinc react with N-substituted 2-oxochromen-3-carboxamides forming ethyl 3-(1a-(R3-carbamoyl)-2-oxo-1a,7b-dihydrocyclopropa[c]chromen-1-yl)-2,2-dialkyl-3-oxopropanoate isomer with a Z-position of methine hydrogens. Zinc enolates prepared from alkyl 2,2-dialkyl-4,4-dibromo-3-oxopentanoates and-hexanoates and zinc react with N-substituted 2-oxochromen-3-carboxamides to give rise to esters of 3-(1-alkyl-1a-(R3-carbamoyl)-2-oxo-1a,7b-dihydrocyclopropa-[c]chromen-1-yl)-2,2-dialkyl-3-oxopropanoic acid as isomers with the E-position of the methine proton and the alkyl substituent. The reaction carried out in the presence of small quantities of THF and HMPA leads to the formation of 9c-alkyl-2-R3-9b,9c-dihydro-5-oxa-2-azacyclopenta[2,3]-cyclopropa[1,2-a]naphthalene-1,3,4-triones. Zinc enolates from alkyl 2,2-dialkyl-4,4-dibromo-3-oxopentanoates and-hexanoates and zinc with the secondary amides of 2-oxochromen-3-carboxylic acid form alkyl 3-(2-oxo-1a-(piperidinocarbonyl)-and 3-(6-R1-1a-(morpholinocarbonyl)-2-oxo-1a,7b-dihydrocyclopropa[c]chromen-1-yl)-2,2-R2,R2-3-oxopropanoates as single geometrical isomers \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (8), 1157.pdf |
R 30 Reaction of alkyl 5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylates with zinc enolates prepared from zinc and 1-arul-2-bromo-2-phenylethanones, 2 bromoindanone, and 2-bromo-6-methyltetralone [Electronic resource] / V. V. Shchepin, A. E. Korzun, M. I. Vakhrin, P. S. Silaichev, M. A. Ezhikova, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 8. - P1169-1173 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Alkyl 5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylates react with zinc enolates prepared from 1-aryl-2-bromo-2-phenylethanones, 2-bromo indanone, 2-bromo-6-methyltetralone and zinc with formation of ethyl 4-(2-aryl-2-oxo-1-phenyl-ethyl)-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylates, alkyl 5,5-dimethyl-2-oxo-4-(1-oxoindan-2-yl)tetrahydrofuran-3-carboxylates, and ethyl 5,5-dimethyl-4-(6-methyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-2-oxotetrahydrofuran-3-carboxylates respectively, mainly as single diastereomers \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (8), 1169.pdf |
C 98 Cyclopropanation of N-substituted 3-aryl-2-cyanoprop-2-enamides and derivatives of 5,5-Dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylic acid and 2-oxochromene-3-carboxylic acid with bromine-containing zinc enolates [Electronic resource] / V. V. Shchepin, P. S. Silaichev, Yu. G. Stepanyan, M. M. Kalyuzhnyi, N. Yu. Russkikh, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 7. - P973-980 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Zinc enolates derived from 1-aryl-2,2-dibromoalkanones react with N-substituted 3-aryl-2-cyanoprop-2-enamides and 5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylic and 2-oxochromene-3-carboxylic acid derivatives to give, respectively, N-substituted 2-alkyl-3-aryl-2-aroyl-1-cyanocyclopropane-1-carboxamides, 6-(4-bromobenzoyl)-4,4,6-trimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester and morpholide, and 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropla[c]chromene-1a-carboxylic acids as a single geometric isomer. Treatment of 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxylic acids with carboxylic acid anhydrides leads to the formation of the corresponding 9c-alkyl-1-aryl-3,4-dioxo-9b,9c-dihydro-2,5-dioxacyclopenta[2,3]cyclopropa[1,2-a]naphthalen-1-yl carboxylates \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (7), 973.pdf |
S 53 Shchepin, V. V. Unexpected formation of 5-aryl-1-benzyl-4-methyl-3,4,2,3-tetrahydro-2,2-dioxospiro[chroman3,3-pyrrol]-4-yl acetates at acylation of 1-aryl-2-benzyl-1-hydroxy-9c-methyl-1,2,9b,9c-tetrahydro-5-oxa-2-azacyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones with acetic anhydride [Electronic resource] / V. V. Shchepin, P. S. Silaichev, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 5. - P778-779 Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (5), 778.pdf |
S 98 Synthesis, Structure, and Keto-Enol Tautomerism of 3-R1-5,5-R2,R2-6-R3-2,3,5,6-Tetrahydropyran-2,4-diones [Electronic resource] / V. V. Shchepin, M. I. Kodess, Yu. Kh. Sazhneva, N. Yu. Russkikh // Russian Journal of General Chemistry. - 2005. - Vol. 75, № 10. - P1622-1627 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Ethyl esters of 2,4-dibromo-2-R1-4-R2-3-oxopentanoic and -hexanoic acids react with zinc and aliphatic or aromatic aldehydes under the conditions of the Reformatskii reaction to give 3-R1-5,5-R2, R2-6-R3-2,3,5,6-tetrahydropyran-2,4-diones, which are obtained in three forms: keto, enol with enolization of the keto group, and enol with enolization of the ester group. The keto form is isolated by crystallization from a mixture of CCl4 and petroleum ether; the first enol form, from MeOH, EtOH, and polar aprotic solvents; and the second enol form, from CHCl3. The second enol form is oxidized in DMSO to form a keto compound containing a hydroxy group at the 3-position of the heteroring \\\\Expert2\\nbo\\Russian Journal of General Chemistry\\2005, V. 75, N 10, p.1622.pdf |
R 30 Reactions of bromine-containing organozinc compounds derived from alfa,alfa-dibromo ketones with 2-arylmethylideneindan-1,3-diones and 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones [Electronic resource] / V. V. Shchepin, Yu. G. Stepanyan, P. S. Silaichev, M. A. Ezhikova, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2010. - Vol. 46, № 4. - P499-502 : il. - Bibliogr. : p. 502 (3 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BROMINE-CONTAINING ORGANOZINC COMPOUNDS -- BROM -- ZINK -- KETONES -- DIONES Аннотация: Bromine-containing organozinc compounds generated from 1,1-dibromo-3,3-dimethylbutan-2-one reacted with 2-arylmethylideneindan-1,3-diones and 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones to give 3-aryl-2-(2,2-dimethylpropanoyl)spiro[cyclopropane-1,2'-indan]-1',3'-diones and 1-aryl-6,6-dimethyl-2-(2,2-dimethylpropanoyl)-5,7-dioxaspiro[2.5]octan-4,8-diones, respectively. Reactions of 2-arylmethylideneindan-1,3-diones with bromine-containing zinc enolates derived from 1-aryl-2,2-dibromopropan-1-ones and 2,2-dibromo-1,2,3,4-tetrahydronaphthalen-1-one resulted in the formation of 2-aroyl-3-aryl-2-methylspiro-[cyclopropane-1,2'-indan]-1',3'-diones and 2,3: 8,9-dibenzo-12-phenyldispiro[4.0.5.1]dodecane-1,4,7-trione, respectively. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2010, 46 (4), 499-502.pdf |