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1.
Yu. V. Tomilov I. V. Kostyuchenko G. P. Okonnishnikova E. V. Shulishov E. A. Yagodkin O. M. Nefedov 《Russian Chemical Bulletin》2000,49(3):472-477
Hydrochlorination of spiro(1-pyrazoline-3,1′-cyclopropanes) proceeds regioselectively at the azocyclopropane group to form 3-(2-haloethyl)pyrazoline derivatives. If the latter contain a halogen atom in the heterocycle, they are readily converted into (2-haloethyl)pyrazole hydrohalides. Bromination of 3-cyanospiro(2-pyrazoline-5,1′-cyclopropane) withN-bromosuccinimide at 20°C proceeds with retention of the cyclopropane ring to form 3-bromo-3-cyanospiro(1-pyrazoline-5,1′-cyclopropane), which is converted into (2-bromoethyl)cyanopyrazole in ∼60% yield at ∼20°C after 3–4 days. 相似文献
2.
Yu. V. Tomilov I. V. Kostyuchenko E. V. Shulishov B. B. Averkiev M. Yu. Antipin 《Russian Chemical Bulletin》2000,49(11):1919-1922
The addition of the phthalimidonitrene fragment, resulting from oxidation ofN-aminophthalimide by lead tetraacetate at −20 to −30°C, to the N=N-bond of 5-bromospirol[l-pyrazolinio-3,1′-cyclopropane]
(1) affords, apart from the stable 5-bromo-N {spiro[l-pyrazolinio-3,1′-cyclopropane]}-N-phthalimidoamide (azimine2), regioisomeric azimine3, which is completely transformed into 3-acetoxy-N-{spiro[l-pyrazolinio-5,1′-cyclopropane]}-N-phthalimidoamide (4) under the reaction conditions. The acetoxy group in this product easily undergoes nuclcophilic substitution on treatment
with McOH, NaN3, or the starting bromopyrazoline1. The structures of azimines obtained were established using NMR spectra, and the structure of the product of reaction of4 with1 was additionally proved by X-ray difraction data.
Published inIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp. 1949–1953, November, 2000. 相似文献
3.
Konstantin L'vovich Obydennov Tatiana Andreevna Kalinina Olga Alexandrovna Vysokova Pavel Alexandrovich Slepukhin Varvara Alexandrovna Pozdina Maria Valer'evna Ulitko Tatiana Vladimirovna Glukhareva 《Acta Crystallographica. Section C, Structural Chemistry》2020,76(8):795-809
The crystal structures of four new chiral [1,2,3]triazolo[5,1‐b][1,3,4]thiadiazines are described, namely, ethyl 5′‐benzoyl‐5′H,7′H‐spiro[cyclohexane‐1,6′‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine]‐3′‐carboxylate, C19H22N4O3S, ethyl 5′‐(4‐methoxybenzoyl)‐5′H,7′H‐spiro[cyclohexane‐1,6′‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine]‐3′‐carboxylate, C20H24N4O4S, ethyl 6,6‐dimethyl‐5‐(4‐methylbenzoyl)‐6,7‐dihydro‐5H‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine‐3‐carboxylate, C17H20N4O3S, and ethyl 5‐benzoyl‐6‐(4‐methoxyphenyl)‐6,7‐dihydro‐5H‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine‐3‐carboxylate, C21H20N4O4S. The crystallographic data and cell activities of these four compounds and of the structures of three previously reported similar compounds, namely, ethyl 5′‐(4‐methylbenzoyl)‐5′H,7′H‐spiro[cyclopentane‐1,6′‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine]‐3′‐carboxylate, C19H22N4O3S, ethyl 5′‐(4‐methoxybenzoyl)‐5′H,7′H‐spiro[cyclopentane‐1,6′‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine]‐3′‐carboxylate, C19H22N4O4S, and ethyl 6‐methyl‐5‐(4‐methylbenzoyl)‐6‐phenyl‐6,7‐dihydro‐5H‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine‐3‐carboxylate, C22H22N4O3S, are contrasted and compared. For both crystallization and an MTT assay, racemic mixtures of the corresponding [1,2,3]triazolo[5,1‐b][1,3,4]thiadiazines were used. The main manner of molecular packing in these compounds is the organization of either enantiomeric pairs or dimers. In both cases, the formation of two three‐centre hydrogen bonds can be detected resulting from intramolecular N—H…O and intermolecular N—H…O or N—H…N interactions. Molecules of different enantiomeric forms can also form chains through N—H…O hydrogen bonds or form layers between which only weak hydrophobic contacts exist. Unlike other [1,2,3]triazolo[5,1‐b][1,3,4]thiadiazines, ethyl 5′‐benzoyl‐5′H,7′H‐spiro[cyclohexane‐1,6′‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine]‐3′‐carboxylate contains molecules of only the (R)‐enantiomer; moreover, the N—H group does not participate in any significant intermolecular interactions. Molecular mechanics methods (force field OPLS3e) and the DFT B3LYP/6‐31G+(d,p) method show that the compound forming enantiomeric pairs via weak N—H…N hydrogen bonds is subject to greater distortion of the geometry under the influence of the intermolecular interactions in the crystal. For intramolecular N—H…O and S…O interactions, an analysis of the noncovalent interactions (NCIs) was carried out. The cellular activities of the compounds were tested by evaluating their antiproliferative effect against two normal human cell lines and two cancer cell lines in terms of half‐maximum inhibitory concentration (IC50). Some derivatives have been found to be very effective in inhibiting the growth of Hela cells at nanomolar and submicromolar concentrations with minimal cytotoxicity in relation to normal cells. 相似文献
4.
Yu. V. Tomilov E. V. Shulishov G. P. Okonnishnikova O. M. Nefedov 《Russian Chemical Bulletin》1995,44(11):2105-2108
Polycyclic spiro(1-pyrazoline-3,1-cyclopropanes) were obtained in 32–70 % yields by the reaction of diazocyclopropane generatedin situ with 2-methyltricyclo[3.2.1.02,4]oct-6-ene, spiro[2,4]hepta-4,6-diene dimer, benzvalene, spiro[2,3]hex-1-ene, methyl 1-methylcyclopropene-3-carboxylate, buta-1,3-diene, and 2-methylbuta-1,3-diene.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2199–2202, November, 1995.This study was financially supported by the Russian Foundation for Basic Research (Grant No. 94-03-08902). 相似文献
5.
A. V. Varlamov A. I. Chernyshev F. I. Zubkov K. F. Turchin A. N. Levov 《Chemistry of Heterocyclic Compounds》2004,40(3):364-369
The cycloaddition of methyl acrylate and ethyl acrylate to 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1'-cyclohexane] N-oxide proceeds without either regiospecificity or stereospecificity. Eight geometrical isomers of spiro[isoxazolidino[3,2-a]benz-2-azepine-5,1'-cyclohexane] were formed, of which several were isolated as pure samples. The cycloaddition of dimethyl acetylenedicarboxylate proceeds stereoselectively, leading to spiro[isoxazolino[3,2-a]benz-2-azepine-5,1'-cyclohexane] with cis arrangement of the protons at C(7) and C(11b). 相似文献
6.
R. I. Khusnutdinov V. A. Dokichev D. K. Galeev N. F. Asylguzhina S. Z. Sultanov U. M. Dzhemilev 《Russian Chemical Bulletin》1988,37(9):1932-1935
1. | Catalytic dimerization of spiro[2.4]hepta-4,6-diene (I) into dispirocyclopropan-5,1'-endotricyclo [5.2.1.02,6]deca-3,8-dien-10,1-cyclopropane (II) was carried out. |
2. | It was established that [Rh(CO)2Cl]2 catalyzes transformation of dispirocyclopropan-6,1'-pentacyclo [5.3.0.02,5.03,9.04,8]-decan-10,1-cyclopropane (XI) into the dimer spiro[2.4]hepta-4,6-diene (II). |
3. | Upon reduction of dispirocyclopropan-6,l'-pentacyclo[5.3.0.02,5.03,9.04.8]decan-<>-cyclopropane in the presence of PtO2 1,1,3,3-tetramethyl-1,3-bishomocubane is formed. |
4. | The possibility of synthesizing adamantane, diamantane, and their derivatives by skeletal isomerization of hydrocarbons obtained from spiro[2.4]hepta-4,6-diene has been shown. |
7.
Yoshihisa Kurasawa Mari Okiyama Yumiko Kamigaki Megumi Kanoh Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1987,24(6):1805-1807
Novel pyrazolo[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzoxazepines 5, 6 and 8 were synthesized, and these compounds were converted into novel spiro[benzoxazole-2′,4(1H,3′H)-pyrazolo[5,1-c][1,2,4]triazines] 7 and 9 by ring transformation. 相似文献
8.
A. V. Varlamov D. G. Grudinin A. I. Chernyshev A. N. Levov I. Yu. Lobanov R. S. Borisov F. I. Zubkov 《Russian Chemical Bulletin》2004,53(8):1711-1716
5-Methyl-4,5-dihydro-3H-spiro[benzo-2-azepine-3,1-cyclohexane] N-oxide was rear- ranged into 5-methyl-1-oxo-1,2,4,5-tetrahydro-3H-spiro[benzo-2-azepine-3,1-cyclohexane]. The latter was used for the synthesis of spiro{triazolo[3,4-a]- and-tetrazolo[5,1-a]benzo-2- azepinecyclohexanes}.Published in Russian in Izvestiya Akademii Nauk.
Seriya Khimicheskaya, No. 8, pp. 1647–1651, August, 2004. 相似文献
9.
Hamdy A. Hammouda Ahmed A. El-Barbary Mohie A. F. Sharaf 《Journal of heterocyclic chemistry》1984,21(4):945-947
5-Amino-3-phenylpyrazole (I) and 5-amino-4-bromo-3-phenylpyrazole (II) reacted with ethyl acetoacetate and acetylacetone to give various pyrazolo[1,5-a]pyrimidines IV-VI and with benzoins to give different fused pyrazoles, namely, imidazo[1,2-b]pyrazoles IX, pyrrolo[2,3-c]pyrazoles X and pyrazolo[4,3-b][1,4]oxazines XII. Diazotized II was coupled with active methylene-containing nitriles to afford pyrazolo[5,1-c]-as-triazines XIV. 相似文献
10.
V. Ya. Sosnovskikh A. Yu. Sizov B. I. Usachev M. I. Kodess V. A. Anufriev 《Russian Chemical Bulletin》2006,55(3):535-542
Reactions of chromones with methyl ketoximes in the presence of lithium diisopropylamide follow the nucleophilic 1,2-addition
mechanism to give spiro[4H-chromene-4,5′-isoxazolines] in good yields. The isoxazoline ring in spiro[4H-chromene-4,5′-isoxazolines] undergoes opening under the action of conc. H2SO4, yielding α,β-unsaturated oximes. Their nitrosation and bromination lead to the corresponding spiroisoxazolines, while the
Beckmann rearrangement, to α,β-unsaturated amides. The latter are also formed directly from spiro[4H-chromene-4,5′-isoxazolines] under the action of PCl5. N-Substituted acetophenone hydrazones in the presence of lithium diisopropylamide react at the C(4) atom of 2-trifluoromethylchromone,
while acetophenone anil under the same conditions, at the C(2) atom.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 516–522, March, 2006. 相似文献
11.
《Journal of heterocyclic chemistry》2017,54(5):2725-2732
New convenient one‐pot method for reduction of hetarenediazonim tetrafluoroborates to the hetarylhydrazine derivatives was developed. Interaction of 8‐carboxyethyl‐3‐(tert‐butyl)‐4‐oxo‐4,6‐dihydropyrazolo[5,1‐c ][1,2,4]triazine‐7‐diazonium tetrafluoroborate with anhydrous SnCl2 in anhydrous CF3CO2H, and further sequence of one‐pot operations led to formation of various derivatives of the unstable ethyl 3‐(tert‐butyl)‐7‐hydrazinyl‐4‐oxo‐4,6‐dihydropyrazolo[5,1‐c ][1,2,4]triazine‐8‐carboxylate (hydrochloride, hydrazides, hydrazones, and pyrazoles), which were isolated in high yields. The anhydrous conditions were first used with SnCl2 and allowed to exclude hydrolysis of the ester group and formation of the by‐products. 相似文献
12.
N. A. Voloshin A. V. Chernyshev A. V. Metelitsa I. M. Raskita E. N. Voloshina V. I. Minkin 《Russian Chemical Bulletin》2005,54(3):705-710
The reaction of 2-hydroxy-3-(4,5-diphenyl-1,3-oxazol-2-yl)-1-naphthaldehyde with 1,2,3,3-tetramethyl-3H-indolium perchlorate afforded photochromic spiro[indoline-2,3′-naphthopyran] containing a 4,5-diphenyloxazole group in position 5′ of the naphthopyran fragment. The merocyanine form of the spiropyran gave complexes with bivalent heavy cations.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 693–697, March, 2005. 相似文献
13.
S. A. Osadchii V. I. Mamatyuk V. G. Shubin A. C. Razus E. Bartha Zs. Arvay 《Russian Chemical Bulletin》1994,43(12):2074-2078
-Cyclopropylalkyl cations of a spiro[2.4]heptane system, which are possible intermediates in solvolytic reactions of the corresponding cyclopropylalkanol derivatives, have been generated from compounds of the spiro(indan-2,1-cyclopropane), spiro(indan-1,1-cyclo-propane), and spiro[acenaphthylene-1(2H),1-cyclopropane] classes under long life conditions (HSO{in3}F-SO{in2}FCl-CD{in2}Cl{in2}, –100 °C).Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2194–2198, December, 1994.This work was carried out with the financial support of the Russian Foundation for Basic Research (Project No. 93-03-4715). 相似文献
14.
Yoshihisa Kurasawa Mari Okiyama Yumiko Kamigaki Megumi Kanoh Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1988,25(4):1259-1262
The reactions of the 3-substituted 4-amino-8-ethoxycarbonyl[5,1-c][1,2,4]triazines 1 and 2 with o-amino-phenol hydrochloride gave the pyrazolo[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzoxazepines 5 and 8 . The alkylation of 5 with methyl iodide and isopropyl iodide afforded the 6-alkoxylpyrazolo[1′,5′:3,4][1,2,4]triazino-[5,6-b][1,5]benzoxazepines 6a and 6b , respectively. Refluxing of 5, 6a, 6b and 8 in hydrochloric acid/acetic acid resulted in ring transformation to produce the spiro[benzoxazole-2′(3′H),4(1H)pyrazolo[5,1-c][1,2,4]-triazines] 7a, 7b and 9 . The screening data of the above compounds was described. 相似文献
15.
Victor M. Chernyshev Dmitry A. Khoroshkin Andrey N. Sokolov Vitaly A. Taranushich Eugene S. Gladkov Svetlana V. Shishkina Oleg V. Shishkin Sergey M. Desenko 《Journal of heterocyclic chemistry》2008,45(5):1419-1427
2′‐Substituted 5′,6′,7′,8′‐tetrahydro‐4′H‐spiro[cyclohexane‐1,9′‐[1,2,4]triazolo[5,1‐b]quinazolines] 3a‐d were synthesized by condensation of 3‐substituted 5‐amino‐1,2,4‐triazoles 1a‐d with 2‐cyclohexylidene cyclohexanone 2 in DMF. The compounds 3 were hydrogenated with sodium borohydride in ethanol to give 2′‐substituted cis‐4a',5′,6′,7′,8′,8a'‐hexahydro‐4′H‐spiro[cyclohexane‐1,9′‐[1,2,4]triazolo[5,1‐b]quinazolines] 4a‐d in high yields. The reactions of alkylation, acylation and sulfonylation of the compounds 4 were studied. The structure of the synthesized compounds was determined on the basis of NMR measurements including HSQC, HMBC, NOESY techniques and confirmed by the X‐ray analysis of 6 and 11b . The described synthetic protocols provide rapid access to novel and diversely substituted hydrogenated [1,2,4]triazolo[5,1‐b]quinazolines. 相似文献
16.
U. M. Dzhemilev R. I. Khusnutdinov Z. S. Muslimov G. A. Tolstikov 《Russian Chemical Bulletin》1987,36(5):977-982
Conclusions Three-component complex cobalt-containing catalysts are proposed, which are activated by PPh3 or by an excess of acetylenic hydrocarbons, with which cyclocodimerization of norbornadiene or spiro{bicyclo[2.2.1]hepta-2,5-diene-7,1-cyclopropane} with diacetylenes can be carried out leading to derivatives of the bitetracyclo[4.3.0.02,4.03,7]nonane series in high yields.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1061–1067, May, 1987. 相似文献
17.
Renate Dworczak 《Monatshefte für Chemie / Chemical Monthly》1991,122(8-9):731-737
Summary The reactivity of cyanomethylene-indolones (1 a–e) and 2-(dicyanomethylene)-indan-1,3-dione (4) towards 1,5-disubstituted 3-pyrazolones (2 a–c) was investigated. The reactions yield spiro[indene- and spiro[indole-4- and 6-pyrano[2,3-c]pyrazoles] (3 a–e,5 a–c). The structures are proven by13C-NMR-spectroscopy. The mechanisms of the reactions are discussed. 相似文献
18.
Yu. V. Tomilov G. P. Okonnishnikova E. V. Shulishov O. M. Nefedov 《Russian Chemical Bulletin》1995,44(11):2114-2117
Strained polycyclic spiro(1-pyrazoline-3,1-cyclopropanes) react with acetyl or benzoyl chlorides at 0–15 °C regioselectively to give in high yields corresponding 1-acyl-3-(2-chloro-ethyl)-2-pyrazolines. Under the same conditions 6-ethenyl-4,5-diazaspiro[2,4]hept-4-ene gives a mixture of two pyrazolines resulting from the acyl group attack directed at different nitrogen atoms. Bicyclic pyrazolines-2 obtained by acylation of the cycloaddition products of diazocyclopropane with 3,3-disubstituted cyclopropenes transform under the action of hydrogen chloride to 1,4,5,6-tetrahydropyridazines in high yields.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2208–2211, November, 1995.The work was carried out with financial support of the Russian Foundation for Basic Research (Grant No. 94-03-08902). 相似文献
19.
Yang Shi Gangqiang Wang Zhiyu Chen Minghu Wu Jian Wang Leslie Trigoura Haibing Guo Yalan Xing Shaofa Sun 《Journal of heterocyclic chemistry》2020,57(4):2044-2047
1,3-Dipolar cycloaddition of isatin N,N′-cyclic azomethine imine catalyzed by CuCO3 has been developed. Structurally interesting heterocyclic spiro(indoline-3,1′-pyrazolo[1,2-a]pyrazoles) have been synthesized as single regioisomers in good yields and high functional group compatibility. 相似文献
20.
V. A. Tartakovsky A. E. Frumkin A. M. Churakov Yu. A. Strelenko 《Russian Chemical Bulletin》2005,54(3):719-725
Thermal cyclization of 3-R-5-chloro-1,2,4-triazoles (R = Cl, Ph) afforded 2,6,10-tri-R- tris[1,2,4]triazolo[1,5-a:1′,5′c:1″,5″-e][1,3,5]triazines 5 (R = Ph) and 7 (R = Cl). These compounds are first representatives of this class of heterocycles, whose structures were unambiguously established. Treatment of these compounds with nucleophiles (H2O/NaOH, NH3) results in the triazine ring opening to give compounds consisting of three 1,2,4-triazole rings linked in a chain. For example, treatment of cyclic compound 5 with aqueous alkali affords 3-phenyl-1-3-phenyl-1-(3-phenyl-1H-1,2,4-triazol-5-yl)-1,2,4-triazol-5-yl-1H-1,2,4-triazol-5-one. Treatment of 3,7,11-triphenyltris[1,2,4]triazolo[4,3-a:4′,3′c:4″,3″-e][1,3,5]triazine (2) with HCl/SbCl5 leads to the triazine ring opening giving rise to 5-(3-chloro-5-phenyl-1,2,4-triazol-4-yl)-3-phenyl-4-(5-phenyl-1H-1,2,4-triazol-3-yl)-1,2,4-triazole. Thermal cyclization of the latter produces 3,7,10-triphenyltris[1,2,4]triazolo[1,5-a:4′,3′c:4″,3″-e][1,3,5]triazine (13). Thermolysis of both cyclic compound 2 and cyclic compound 13 is accompanied by the Dimroth rearrangement to yield 3,6,10-triphenyl-tris[1,2,4]triazolo[1,5-a:1′, 5′-c:4″,3″-e][1,3,5]triazine (14). Compounds 13 and 14 are the first representatives of cyclic compounds with this skeleton. 13C NMR spectroscopy allows the determination of the isomer type in a series of tris[1,2,4]triazolo[1,3,5]triazines.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 706–712, March, 2005. 相似文献