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1.
Carol Pérez-Casas Shofiur Rahman Nazneen Begum Zeng Xi Takehiko Yamato 《Journal of inclusion phenomena and macrocyclic chemistry》2008,60(1-2):173-185
A novel ditopic receptor possessing two complexation sites such as crown ether and 2-pyridylmethyl groups bearing 1,3-alternate conformation based on thiacalix[4]arene was prepared. The binding behaviors with Li+ and Ag+ have been examined by 1H NMR titration experiment. The exclusive formation of mononuclear complexes of 1,3-alternate-5 with Li+ and Ag+ was observed even though the formation of the heterogeneous dinuclear complexes was expected. The decomplexation of Li+ from the crown moiety of 1:1 complex 1,3-alternate-5?Li+ to form the Ag+?1,3-alternate-5 complex by addition of AgSO3CF3 clearly shows that pyridyl moiety works as an efficient switch-off of the recognition ability of the crown moiety. We have also developed the construction of hydrogen-bonding self-assembly heterodimeric systems based on bis(4-pyridyl) and dicarboxylic acid thiacalix[4]arene derivatives in 1,3-alternate conformation. Their supramolecular behaviors are studied by 1H NMR titration experiments with K+ and Ag+ ions. Although the values of the dimerization constants are relatively small, the stability of the dimers is strong enough to overcome only small conformational changes upon complex formation. 相似文献
2.
R. I. Vas’kevich A. I. Vas’kevich E. B. Rusanov V. I. Staninets M. V. Vovk 《Russian Journal of Organic Chemistry》2013,49(1):123-129
Intramolecular electrophilic cyclization of 6-allylsulfanylpurine by the action of iodine and arenesulfenyl chlorides gave 7-iodomethyl-7,8-dihydro[1,3]thiazolo[2,3-i]purin-6-ium pentaiodide and 7-arylsulfanylmethyl-7,8-dihydro[1,3]thiazolo[2,3-i]purin-6-ium perchlorates, respectively. 7-Iodomethyl-7,8-dihydro-[1,3]thiazolo[2,3-i]purin-6-ium iodide reacted with sodium and potassium alkoxides to produce alkyl N-[5-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-4-yl]formimidates, and its reaction with secondary cyclic amines afforded 5-(4-methyl-1,3-thiazol-2-yl)-N-[morpholin-4-yl(or piperidin-1-yl)methylidene]-1H-imidazol-4-amines. Successive treatment of 7-arylsulfanylmethyl-7,8-dihydro[1,3]thiazolo[2,3-i]purin-6-ium perchlorates with sodium acetate and morpholine led to the formation of 5-(4-arylsulfanylmethyl-4,5-dihydro-1,3-thiazol-2-yl)-N-(morpholin-4-ylmethylidene)-1H-imidazol-4-amines. 相似文献
3.
A. V. Borisov Zh. V. Matsulevich V. K. Osmanov G. N. Borisova A. D. Samsonova A. O. Chizhov 《Russian Chemical Bulletin》2012,61(3):678-679
Cycloaddition of 1,3-benzothiazole-2-selenenyl chloride to alkenes leads to 2,3-dihydrobenzo[d][1,3]selenazolo[2,3-b][1,3]thiazolium-4 derivatives. 相似文献
4.
In this work, we described an easy preparation of substituted 4-amino-5-cyano-1,3-thiazoles. These compounds have been used as starting materials to obtain two classes of compounds. New substituted [1,3]thiazolo[4,5-e]pyridines were synthesized in one step via Friedländer reaction. Diazotation of 4-amino-5-cyano-1,3-thiazoles afforded 4-chloro[1,3]thiazolo[4,5-d][1,2,3]triazines in one step. The later was substituted by a secondary amine to obtain substituted 4-amino[1,3]thiazolo[4,5-d][1,2,3]triazines. 相似文献
5.
In the present study, two novel calix[4]arene receptors containing triphenylamine units in 1,3-alternate conformation have been synthesized and characterized in detail. First, the 25,27-dipropoxy-26,28-bis[(3-aminopropyl)oxy]-calix[4]arene 4 and 25,26,27,28-tetra[(3-aminopropyl)oxy]-calix[4]arene 7 were prepared by using convenient reagents. Then, these amino derivatives of calix[4]arene were converted to Schiff base derivatives appended to triphenylamine of calix[4]arene (5 and 8) using 4-formyltriphenylamine via condensation. The 1,3-alternate conformation of the synthesized calix[4]arenes was determined by 1H and 13C NMR analyses. Also, their structures have been characterized by using 1H and 13C NMR, infrared, and elemental analyses. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file. 相似文献
6.
Magdi E.A. Zaki A. Paula Bettencourt Francisco M. Fernandes M. Fernanda Proença 《Tetrahedron》2012,68(24):4628-4634
Substituted 4-(2,5-dihydro-1H-pyrrol-3-yl)-1H-imidazoles were prepared from 5-amino-1-aryl-4-cyanoformimidoylimidazoles and cyanoacetamide, under mild experimental conditions. The pyrrolyl-imidazoles were cyclized to the corresponding 7,8-dihydroimidazo[4,5-b]pyrrolo[3,4-d]pyridines by reflux in ethanol, with catalysis by DBU. The same pyrrolyl-imidazoles were reacted with orthoesters, at room temperature and in the presence of sulfuric acid, to generate 3,7-dihydro-8H-imidazo[4,5-d]pyrrolo[3,2-f]diazepines in very good yield. Electrochemical studies of the imidazo[4,5-d]pyrrolo[3,2-f][1,3] diazepine derivatives were carried out. The reduction potential of 7-ethyl-3-(4-methoxyphenyl)-8-oxo-7,8-dihydro-3H-imidazo[4,5-d]pyrrolo[3,2-f][1,3] diazepine-9-carbonitrile was in the adequate range for presenting bioreduction properties. 相似文献
7.
Takehiko Yamato Carol Pérez-Casas Shofiur Rahman Zeng Xi Mark R. J. Elsegood Carl Redshaw 《Journal of inclusion phenomena and macrocyclic chemistry》2007,58(1-2):193-197
A novel receptor possessing two complexation sites and bearing 1,3-alternate conformation based on thiacalix[4]arene, confirmed by single crystal X-ray analysis, was prepared. The tetrathiacalix[4]arene
diamide shows strong intramolecular hydrogen bonding. The binding behavior towards K+ and halides has been examined by 1H NMR titration experiments. 相似文献
8.
Dmitriy V. Maltsev Alexander A. Spasov Pavel M. Vassiliev Maria O. Skripka Mikhail V. Miroshnikov Andrey N. Kochetkov Nataliya V. Eliseeva Yuliya V. Lifanova Tatyana A. Kuzmenko Lyudmila N. Divaeva Anatolii S. Morkovnik 《Molecules (Basel, Switzerland)》2021,26(19)
A number of novel 2,3,4,5-tetrahydro[1,3]diazepino[1,2-a]benzimidazole derivatives 2 were obtained by alkylation mainly in the 1H-tautomeric form of 2,3,4,5-tetrahydro[1,3]diazepino[1,2-a]benzimidazole or its 8,9-dimethyl-substituted analog 4-chlorobenzyl bromide, 4-chloroacetic acid fluoroanilide, and 4-tert-butylphenacyl bromide in neutral medium. Compounds 3 were cyclized and synthesized earlier with 11-phenacyl-substituted diazepino[1,2-a]benzimidazoles upon heating in conc. HBr. The chemical structures of the compounds were clarified by using the 1H Nuclear Magnetic Resonance Spectroscopy (1H-NMR) technique. Anxiolytic properties were evaluated using the elevated plus maze (EPM) and open field (OF) tests. The analgesic effect of compounds was estimated with the tail flick (TF) and hot plate (HP) methods. Besides, possible the influence of the test compounds on motor activities of the animals was examined by the Grid, Wire, and Rotarod tests. Compounds 2d and 3b were the most active due to their prominent analgesic and anxiolytic potentials, respectively. The results of the performed in silico analysis showed that the high anxiolytic activity of compound 3b is explained by the combination of a pronounced interaction mainly with the benzodiazepine site of the GABAA receptor with a prominent interaction with both the specific and allosteric sites of the 5-HT2A receptor. 相似文献
9.
P. Thuéry M. Nierlich C. Bressot V. Lamare J. F. Dozol Z. Asfari J. Vicens 《Journal of inclusion phenomena and macrocyclic chemistry》1995,23(4):305-312
The crystal structures of two binuclear complexes between caesium and 1,3-calix[4]-bis-crowns have been determined. Cs2
Bis-benzoC6(NO3)2. 3CHCl3 (1) in whichBis-benzoC6 is 1,3-calix[4]-bis-benzo-crown-6, crystallizes in the orthorhombic system: space groupPca2
1 a=19.513(10),b=15.382(5),c=23.708(9) Å,V=7116(5) Å3,Z=4. Refinement led to a final conventionalR value of 0.065 for 2321 reflections. The structure of (1) is analogous to those already reported withBis-C6, (in whichBis-C6 is, 1,3-calix[4]-bis-crown-6) and NO
3
–
as a counter-ion. Cs2
Bis-C6(NCS)2 (2) crystallizes in the monoclinic system: space, groupC2 a=36.57(2),b=11.47(1),c=13.65(1) Å, =109.03(5)°.,V=5415(6) Å3,Z=4. Refinement led to a final conventionalR value of 0.063 for 2227 reflections. Compound (2) is made of dimers bridged by a disordered NCS– ion. The crown ether chain conformations are discussed.
Supplementary data relating to this article (atomic coordinates, anisotropic displacement parameters, bond distances and angles and observed and calculated structure factors) are deposited with the British Library as Supplementary Publication No. SUP 82199 (52 pages). 相似文献
10.
G. V. Mokrov A. M. Likhosherstov V. P. Lezina T. A. Gudasheva I. S. Bushmarinov M. Yu. Antipin 《Russian Chemical Bulletin》2011,60(8):1694-1702
Reactions of methyl 2-(2-formyl-1H-pyrrol-1-yl)alkanoates with unsubstituted aliphatic 1,2-, 1,3-, and 1,4-diamines gave N-unsubstituted pyrrolo[2,1-c]-1,3-diazacycloalkano[1,2-a]-pyrazinones. Some of them show ring-chain tautomerism. Transformations of these compounds led to a number of novel heterocyclic systems: 2,10-dihydro-3H,5H-imidazo[1,2-a]-pyrrolo[1,2-d]pyrazines, 2,3,4,11-tetrahydro-6H-pyrrolo[1??,2??:4,5]pyrazino[1,2-a]pyrimidines, 1,2,3,5,6,10b-hexahydroimidazo[1,2-a]pyrrolo[2,1-c]pyrazines, 1,3,4,6,7,11b-hexahydro-2H-pyrrolo[2??,1??:3,4]pyrazino[1,2-a]pyrimidines, and 2,3,4,5,6,7-hexahydro-1H-pyrrolo[2,1-c]-[1,4,7]triazacycloundecin-8(9H)-one. 相似文献
11.
1,3-Alternate calix[4]arenes, decorated with four nonpolar ‘all-trans’ tetracyclic nuclei and cation-stabilizing β-methoxyethoxy appendages, were synthesized from commercially available starting materials and through straightforward functional groups transformations/couplings. Their Na+-transport activities, when compared with those exerted by the known conformationally-rigidified 1,3-alternate calix[4]arene AB/cis cholic acid conjugates, suggest that the cation conductance is related to the morphology of the pendant steroids. 相似文献
12.
Summary The reaction of 3,4-methylenedioxycinnamic acid (1) with thionyl chloride resulted in the formation of 7-chlorothieno[2,3-f]-1,3-benzodioxole-6-carbonyl chloride (2) and cinnamoyl chloride (3). Subsequent reaction of the former withp-substituted anilines led to the formation of 7-chloro-N-(p-substituted phenyl)-thieno[2,3-f]-1,3-benzodioxole-6-carboxamides (4a–c) which on photocyclization afforded 2-substituted [1,3]dioxolo[5,6][1]benzothieno[2,3-c]quinolin-6(5H)-ones (5a–c) in fairly good yields and high purity. The structures have been confirmed by IR,1H NMR, and analytical methods.Accepted for presentation at the Hong Kong International Symposium on Heterocyclic Chemistry (August 13–16, 1995) 相似文献
13.
Piergiorgio Pecorari Marcella Rinaldi Maria Paola Costi 《Journal of heterocyclic chemistry》1989,26(6):1701-1705
Derivatives of two new molecular structures, namely, [1,3]thiazino[3,2-a]purine and [1,2,3]triazolo[4,5-d]-[1,3]thiazino[3,2-a]pyrimidine, were synthesized together with other heterocyclic compounds. Retrosynthetic analysis of their molecular skeletons suggested a simple way of obtaining 3,4-dihydro-7,8-diamino-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one, which is a useful intermediate for their synthesis. This intermediate and the thiazole homologue were obtained directly by reaction of 5,6-diamino-2,3-dihydro-2-thioxo-4(lH)-pyrimidi-none with 1,3- or 1,2-dibromoalkane, respectively. 相似文献
14.
Qiuping Ding Xianjin Liu Jinsheng Yu Qiulan Zhang Dan Wang Banpeng Cao Yiyuan Peng 《Tetrahedron》2012,68(21):3937-3941
Tandem addition-cyclization reactions of various 2-alkynylbenzenamines with CS2 lead to the formation of 2-mercapto-4-benzylidene-4H-benzo[d][1,3]thiazines under mild conditions. The reactions showed moderate to excellent yields and were highly regiospecific, and only the six-membered ring was generated via 6-exo-dig S-cyclization. The reaction can be transferred to highly functionalized 4-benzylidene-4H-benzo[d][1,3]thiazines via CuI-catalyzed crossing-coupling and reductive coupling reactions. 相似文献
15.
Xin-long Ni Hirotsugu Tomiyasu Tomoe Shimizu Carol Pérez-Casas Zeng Xi Takehiko Yamato 《Journal of inclusion phenomena and macrocyclic chemistry》2010,67(1-2):99-108
A novel thiacalix[4]arene ditopic receptor with 1,3-alternate conformation and possessing two complexation sites for hard and soft cations, 5,11,17,23-tetra-tert-butyl-25,27-bis[(N,N-diethylaminocarbonyl)methoxy]-26,28-bis[(pyridylmethyl)oxy]-2,8,14,20-tetrathiacalix[4]arene is prepared. Regioselective synthesis of distal-bis[(N,N-diethylaminocarbonyl)methoxy]thiacalix[4]arene is accomplished by a protection-deprotection method using benzyl groups as a protecting group. The deprotection of benzyl group was succeeded in the presence of solid superacid (Nafion-H) under refluxing benzene. Its complexation behavior is examined by 1H-NMR titration experiments. The formation of 1:2 homo- and heteronuclear complexes demonstrates that the preorganization, subtle conformational changes and affinity have a pronounced effect on the complexation of the receptor. 相似文献
16.
Carol Pérez Casas Takehiko Yamato 《Journal of inclusion phenomena and macrocyclic chemistry》2005,53(1-2):1-8
Direct O-alkylation of p-tert-butyltetrathiacalix[4]arene with N,N-diethylchloroacetamide afforded two conformational isomers (1,3-alternate and cone) of tetrakis[(N,N-diethylaminocarbonyl)methoxy]thiacalix[4]arene and 1,3-disubstituted bis[(N,N-diethylaminocarbonyl)methoxy]thiacalix[4]arene, depending on the base used. The complaxation behaviors of the tetrakis isomers
were assessed by 1H NMR titration experiments. Evidence of 1:2 (homo- and hetero-dinuclear) complexes formation of 1,3-alternate-tetrakis[(N,N-diethylaminocarbonyl)methoxy]thiacalix[4]arene with alkali (K+ and Na+) or transition (Ag+) metal ions was obtained. Interestingly, it was found that the cone-tetrakis[(N,N-diethylaminocarbonyl)methoxy]thiacalix[4]arene required a prior Ag+ complexation to form 1:2 heterodinuclear complex.
Received in final form: 26 January 2005 相似文献
17.
Matthias HeydenreichAndreas Koch László LázárIstván Szatmári Reijo SillanpääErich Kleinpeter Ferenc Fülöp 《Tetrahedron》2003,59(11):1951-1959
Starting from the 1′- or 2′-phenyl-substituted 1-(2′-hydroxyethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline diastereomers 3 and 6, 4-unsubstituted and 4-(p-nitrophenyl)- and 4-oxo-substituted 1-phenyl- and 2-phenyl-9,10-dimethoxy-2H,4H-1,6,7,11b-tetrahydro-1,3-oxazino[4,3-a]isoquinolines (7-12) were prepared. The relative configurations and the predominant conformations of the products were determined by NMR spectroscopy, by quantum chemical calculations and, for (2R∗,4S∗,11bR∗)-9,10-dimethoxy-4-(p-nitrophenyl)-2-phenyl-2H,4H-1,6,7,11b-tetrahydro-1,3-oxazino[4,3-a]isoquinoline (11), by X-ray diffraction. 相似文献
18.
Jiří Dybal Emanuel Makrlík Petr Vaňura Jan Budka 《Monatshefte für Chemie / Chemical Monthly》2008,139(10):1175-1178
From extraction experiments in the two-phase water-nitrobenzene system and γ-activity measurements, the stability constant
of protonated 1,3-alternate-25,27-bis(1-octyloxy)calix[4]arene-crown-6 in nitrobenzene saturated with water was determined. By using DFT calculations,
the most probable structure of the 1,3-alternate-25,27-bis(1-octyloxy)calix[4]arene-crown-6 · H3O+ complex species was derived.
Correspondence: Emanuel Makrlík, Faculty of Applied Sciences, University of West Bohemia, Pilsen, Czech Republic. 相似文献
19.
Lidia S. Konstantinova 《Tetrahedron》2009,65(11):2178-2183
Treatment of N-substituted 2-methyl-1H-indoles 1 with S2Cl2 and DABCO in chloroform gave the corresponding [1,2]dithiolo[4,3-b]indole-3(4H)-thiones 5 by the addition of triethylamine in high yield. 1,2-Dithiole-3-thiones 5 underwent cycloaddition with one or two DMAD equivalents to afford either 2-(3-thioxo-1,3-dihydro-2H-indol-2-ylidene)-1,3-dithioles 10 or fused 4,5-dihydrothiopyrano[3,2-b]indoles 9. 相似文献
20.
K. Bogdanowicz-Szwed M. Krasodomska 《Monatshefte für Chemie / Chemical Monthly》1996,127(12):1273-1281
Summary Reaction of 1,3-diaza-1,3-butadienes (1a–c) with various ketenes and chloroketenes results in the formation of substituted 4-oxo-pyrimido[2,1-b]benzothiazoles (4a–d) and 1,3,4-thiadiazolo[3,2-a]pyrimido-4-ones (4e,f). Reaction of 1,3-diaza-1,3-butadienes1d,e with ketenes and chloroketenes leads to the 2-morpholine-substituted compounds7 and15, respectively. All reactions proceedvia formation of [4+2] cycloadducts that eliminate methylthiol, methylsulfenyl chloride, or morpholine.
Hetero-Diels-Alder-Reaktion einiger 1,3-Diaza-1,3-butadiene mit Ketenen. Synthese funktionalisierter Pyrimido[1,2-b]benzothiazole und 1,3,4-Thiadiazolo[3,2-a]pyrimidine
Zusammenfassung Die Reaktion der 1,3-Diaza-1,3-butadiene1a–c mit verschiedenen Ketenen und Chlorketenen führt zu substituierten 4-Oxo-pyrimido[2,1-b]benzothiazolen (4a–d) und 1,3,4-Thiadiazolo[3,2-a]pyrimido-4-onen(4e,f). Die 1,3-Diaza-1,3-butadiene1d,e ergeben mit Ketenen und Chlorketenen die 2-Morpholin-substituierten Verbindungen7 und15. Alle Reaktionen verlaufen über [4+2]-Cycloaddukte, die Methylthiol, Methylsulfenylchlorid oder Morpholin eliminieren.相似文献