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1.
Hydroboration of trialkyn-1-yl(organo)silanes with one equivalent and two equivalents of 9-borabicyclo[3.3.1]nonane, 9-BBN
afford dialkyn-1-ylsilanes and alkyn-1-ylsilanes, respectively. The alkyn-1-ylsilane derivatives are stable at room temperature
and can be store under dry argon for prolong period of time. These compounds are attractive materials for further rearrangements
to afford novel 1-silacyclobutene derivatives bearing Si-alkenyl or Si-alkynyl functionalities. The hydroboration reaction
is well controlled by the Si-R1 function, i.e., the starting silanes with R1 = Ph selectively afford hydroboration of one Si-C≡C bond with one equivalent of 9-BBN, leaving the other two functionalities
untouched. Under mild reaction conditions (25°C), the starting silanes with R1 = Me lead to mixture containing dialkyn-1-ylsilane, alkyn-1-ylsilane and their respective 1-silacyclobutene derivatives.
All new compounds are sensitive towards air and moisture and were studied by multinuclear magnetic resonance spectroscopy
(1H, 13C, 11B, 29Si NMR) in solution. 相似文献
2.
The quantitative and fully stereoselective synthesis of (Z)-perfluoroalkyl-1-iodo-1-triisopropylsilylalkenes and their easy, high-yielding transformation into the corresponding 1-iodo-2-perfluoroacetylenes and (Z)-2-perfluoroalkyl-1-iodo-1-alkenes, compounds of interest as synthons for classical organometallic chemistry or for metal-catalyzed coupling reactions, are discussed. 相似文献
3.
M. A. KirpichËnok L. Yu. Fomina I. I. Grandberg 《Chemistry of Heterocyclic Compounds》1991,27(5):482-491
The reaction of 3-iodo-7-diethylaminocoumarin and 2,3,6,7-tetrahydro-10-iodo-1H,5H-quinolizino[9,9a,1-gh]coumarin with secondary amines (diethylamine, piperidine, morpholine, imidazole, and benzimidazole) leads to 4,7-diaminocoumarins. The corresponding 3-iodo-4-chloro-7-dialkylaminocoumarins under similar conditions give 3-iodo-4,7-diaminocoumarins. 4-Aminomethyl derivatives of coumarins are formed in the reactions of 3-iodo-4-methyl-7-diethylaminocoumarin and 2,3,6,7-tetrahydro-9-methyl-10-iodo-1H,5H-quinolizino[9,9a,1-gh]coumarin with these secondary amines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 609–618, May, 1991. 相似文献
4.
《Tetrahedron letters》1986,27(7):775-778
The reaction of 1-iodo-3-bromopropene derivatives (1) with lithium enolates of N,N-dialkylcarboxamides followed by treatment of the allylation product (2) with two equiv of t-BuLi cleanly provides cyclopentenones in high yields, while the corresponding cycliacylation reaction of 6-iodo-5-hexenamides provides cyclohexenones. 相似文献
5.
Attila Takács 《Tetrahedron》2010,66(25):4479-1040
Iodoarenes (iodobenzene and 2-iodothiophene) and iodoalkenes (1-iodocyclohexene, 1-iodo-4-tert-butylcyclohexene, 1-iodo-2-methylcyclohexene and 1-iodo-1-(1-naphthyl)ethene) were used as substrates in palladium-catalysed aminocarbonylation with N,O-dimethylhydroxylamine. The corresponding Weinreb amides were prepared in high isolated yields (up to 87%) when forcing conditions (40-60 bar of CO, 50 °C) were used. The aminocarbonylation provides the Weinreb amides as pure products in a chemoselective reaction. No formation of ketocarboxamides, due to double CO insertion, except for 2-iodothiophene, was observed even at 60 bar of CO pressure. 相似文献
6.
4-Methyl- and 4-benzyl-5-aminoisoquinolin-1-ones are close analogues of the water-soluble PARP-1 inhibitor 5-AIQ. Their synthesis was approached through Pd-catalysed cyclisations of N-(2-alkenyl)-2-iodo-3-nitrobenzamides. Reaction of N,N-diallyl-2-iodo-3-nitrobenzamide with Pd(PPh3)4 gave a mixture of 2-allyl-4-methyl-5-nitroisoquinolin-1-one and 2-allyl-4-methylene-5-nitro-3,4-dihydroisoquinolin-1-one. N-Benzhydryl-N-cinnamyl-2-iodo-3-nitrobenzamide similarly gave 2-benzhydryl-4-benzyl-5-nitroisoquinolin-1-one and 2-benzhydryl-4-benzylidene-5-nitro-3,4-dihydroisoquinolin-1-one. The isomeric products are not interconvertible. A deuterium-labelling study indicated that the isomers were formed by different pathways: a π-allyl-Pd route and the classical Heck route. The corresponding secondary amides N-allyl-2-iodo-3-nitrobenzamide and N-((substituted)-cinnamyl)-2-iodo-3-nitrobenzamide gave good yields of the required 4-methyl- and 4-((substituted)-benzyl)-5-nitroisoquinolin-1-ones, respectively, under optimised conditions (Pd(PPh3)4, Et3N, Bu4NCl, 150 °C, rapid heating). Hydrogenation of the nitro groups gave 4-methyl- and 4-benzyl-5-aminoisoquinolin-1-ones, which were potent inhibitors of PARP-1 activity. 相似文献
7.
Exposure of 1-alkenyl(phenyl)- and 1-alkynyl(phenyl)-λ3-iodanes to THF at room temperature in the presence of a catalytic amount of trialkylborane results in smooth reduction to give 1-iodo-1-alkenes and 1-iodo-1-alkynes as major products, respectively. The key step in the reductions probably involves a single-electron transfer from α-tetrahydrofuryl radical to the λ3-iodanes, which generates the labile [9-I-2] iodanyl radicals. 相似文献
8.
9.
7-Iodo- and 7,8-diiodo-4-(3-dimethylaminopropylamino)quinolines and 7-iodo-4-(3) dipropyl-aminopropylamlno)- and 7-iodo-4-(3-diallylaminopropylamino)quinoline were obtained by the reaction of 7-iodo- and 7,8-diodo-4-chloroquinolines with the corresponding diamines. The catalytic hydrogenation of 7-iodo-4-(3-diallylaminopropylamino)quinoline at normal pressure leads to 7-iodo-4-(3-dipropylaminopropylamino)quinoline.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 972–975, July, 1980. 相似文献
10.
R. R. Gataullin F. F. Minnigulov T. V. Khakimova A. A. Fatykhov L. V. Spirikhin I. B. Abdrakhmanov 《Russian Chemical Bulletin》2002,51(7):1329-1331
The reactions of 2-(cyclohex-2-enyl)-4,5-difluoroaniline or N-methyl-2-(cyclohex-2-enyl)aniline with I2 in CCl4 in the presence of NaHCO3 give 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazoles, which isomerize in MeCN into the corresponding 3-iodo-2,4-propano-1,2,3,4-tetrahydroquinolines in quantitative yields. 相似文献
11.
Attila Takács 《Tetrahedron》2008,64(37):8726-8730
The high-yielding synthesis of novel N-acyl phosphonates with unprecedented structure was carried out by a homogeneous carbonylation reaction under mild reaction conditions. The palladium-catalysed aminocarbonylation of iodoalkenes (1-iodo-cyclohexene, 1-iodo-4-tert-butyl-cyclohexene, 1-iodo-2-methyl-cyclohexene and α-iodostyrene) with diethyl α-aminobenzyl-phosphonate as N-nucleophile resulted in the exclusive formation of carboxamides. The same reaction with iodoaromatics (iodobenzene, 2-iodothiophene) provided the corresponding carboxamide in high yields and some 2-keto-carboxamides as side products due to single and double carbon monoxide insertion, respectively. 相似文献
12.
Subramanian Venkataraman 《Tetrahedron letters》2006,47(41):7317-7322
Pd/C-Cu catalyzed coupling reactions of 3-iodo-1H-quinolin-4-ones with a variety of terminal alkynes afforded furo[3,2-c]quinolines regioselectively in good to excellent yields. 3-Alkynyl quinolones were isolated under the same reaction conditions when the nitrogen of 3-iodo-1H-quinolin-4-one was substituted with an alkyl group. 相似文献
13.
In order to investigate synthetic route of polyperfluorotriazine elastomer, 2-trifluoromethyl4,6-bis(4′-iodo-2′-oxahexafluorobutyl)-1,3,5-triazine (1), a novel triazine monomer, was synthesized from 5-iodo-3-oxa-octafluoropentanesulfonyl fluoride (2) in eight-steps. 2 was reduced by potassium sulfite to the sulfinate (3), which was treated with hydriodic acid to yield 5-iodo-3oxa-hexafluoropentanoic acid (4). Compound 4 was transformed to 5-iodo-3-oxa-hexafluoropentanenitrile (7) through the corresponding ester 5 and amide 6. The desired product 1 was prepared by acylation-cyclodehydration of the imidoylamidine 9, obtained by condensation of the nitrile 7 with the amidine 8.The various methods for the esterification of perfluorocarboxylic acid were studied and a possible mechanism for the transformation of perfluorosulfinate to the corresponding perfluorocarboxylic acid by hydriodic acid was proposed.Crude 1 contained compounds 6, 11, 13, as impurities which were removed by low temperature crystallization followed by filtration through a short alumina column. The monomer 1 was polymerized by UV-irradiation in the presence of Hg with or without solvent. Polyperfluorooxaalkyl triazine 17 thus obtained showed good thermal stability. In the main chain of the polymer there was no weak unit of the uncyclized ring. Polymer 17 had an average molecular weight of ca. 1.33—2.0×10~4 (D. P.=27—42) and the temperature of 10% weight loss in nitrogen was 340℃. 相似文献
14.
Attila Takács 《Tetrahedron》2009,65(25):4795-4483
Two highly reactive iodoalkenes (1-iodo-1-(2-naphthyl)ethene and 1-iodo-1-(1-naphthyl)ethene) were prepared from the corresponding acetonaphthone isomers via their hydrazones and used as substrates in palladium-catalysed carbonylations. Both iodoalkenyl substrates proved to be highly reactive in the presence of various N-nucleophiles and the corresponding N-substituted naphthylacrylamides were formed chemoselectively in nearly quantitative yields. High isolated yields (up to 93%) were achieved with all types of amines under mild reaction conditions. The alkoxycarbonylation of the above iodoalkenes resulted in esters of unexpectedly good isolated yields (up to 77%). 相似文献
15.
Jos M. García Fernndez Carmen Ortiz Mellet M. Angeles Pradera Adrin Jos Fuentes Mota 《Journal of heterocyclic chemistry》1991,28(3):777-780
The syntheses of N-(trans-2-iodocyclohexyl)- 1–4 , N-(2-iodo-3,3-dimethylbutyl) 5 , and N-(2-iodo-1,1-diphenylethyl)ureas 6, 7 and the cyclization of 6 and 7 into 2-amino-2-oxazoline derivatives 8, 9 are reported. The structures of prepared compounds are based on analytical and spectroscopic data. 相似文献
16.
R. R. Gataullin F. F. Minnigulov L. V. Spirikhin I. B. Abdrakhmanov 《Russian Journal of Organic Chemistry》2004,40(7):986-991
Iodination of N-isopropyl- and N-benzyl-2-(2-cyclohexenyl)anilines gave the corresponding 1-iodo-hexahydrocarbazoles which underwent quantitative isomerization into 3-iodo-2,4-propano-1,2,3,4-tetrahydro-quinolines. Nucleophilic substitution in 1-iodohexahydrocarbazoles and 3-iodo-2,4-propano-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole was studied. N-Allylation of the latter via reaction with allyl bromide is accompanied by replacement of the iodine atom by bromine. 相似文献
17.
Molchanov A. P. Stepakov A. V. Boitsov V. M. Kopf J. Kostikov R. R. 《Russian Journal of Organic Chemistry》2003,39(1):108-114
Substituted methyl 2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylates and 1,2,7-triazaspiro[4.4]non-2-ene-3-carboxylates react with N-iodosuccinimide (or the system iodine-silver trifluoroacetate) to give, respectively, methyl 6-iodo-3-azabicyclo[3.1.0]hexane-6-carboxylates or methyl 1-iodo-4,6-dioxo-5-azaspiro[2.4]heptane-1-carboxylates as mixtures of exo and endo isomers. 相似文献
18.
Acetoxymercuration of a series of acylferrocenes has been found to produce appreciable amounts of 1,2- as well as 1,1′-mercurated products. The mercurated derivatives were readily converted into a variety of other unsymmetrical 1,2- and 1,1′-disubstituted ferrocenes. The 1,2-orientation of substituents was inferred by spectra data, and was confirmed by a comparison of products from the mercuration reactions with analogous products obtained from the 2-lithiation of [(dimethylamino)methyl]ferrocene. Both 2-(methoxycarbonyl)biferrocene and 2-acetylbiferrocene have been obtained from mixed Ullmann reactions of iodoferrocene with 2-iodo-1-(methoxycarbonyl)ferrocene and 2-iodo-1-acetylferrocene, respectively. 相似文献
19.
V. F. Mironov E. N. Varaksina A. A. Shtyrlina R. Z. Musin A. I. Konovalov 《Russian Journal of Organic Chemistry》2006,42(1):118-123
According to NMR data, the reaction of 2,2,2-trichloro-1,3,2λ5-benzodioxaphosphole with 1-iodo-2-phenylethyne leads to formation of 2,6-and 2,8-dichloro-3-iodo-4-phenyl-1,2λ5-benzoxaphosphinine 2-oxides which undergo partial hydrodeiodination to 2,6-and 2,8-dichloro-4-phenyl-1,2λ5-benzoxaphosphinine 2-oxides, respectively. 相似文献
20.
Safronov AV Sevryugina YV Jalisatgi SS Kennedy RD Barnes CL Hawthorne MF 《Inorganic chemistry》2012,51(4):2629-2637
8-Iodo-1,2-dicarba-closo-dodecaborane (7) was prepared in three steps starting from decaborane-14 with 20% overall yield. In the presence of nucleophiles, compound 7 undergoes selective removal of the boron vertex in the position para to the iodine substituent to form the anionic nido-carborane 1-iodo-7,8-dicarba-nido-undecaborate. Capping of the corresponding dicarbollide dianion with BI(3) led to formation of the new carborane, 3,10-diiodo-1,2-dicarba-closo-dodecaborane (15). The same dicarbollide dianion reacts with cobalt and nickel acetylacetonates in anhydrous tetrahydrofuran to form the corresponding bis(dicarbollide) complexes with excellent yields. All compounds were characterized by multinuclear NMR and high-resolution mass spectroscopy. Structures of 2-iododecaborane (2), 8-iodo-1,2-dicarba-closo-dodecaborane (7), 1-ethoxycarbonyl-8-iodo-1,2-dicarba-closo-dodecaborane (10), cesium 1-iodo-7,8-dicarba-nido-undecaborate (13), 3,10-diiodo-1,2-dicarba-closo-dodecaborane (15), and cesium 3,3'-commo-(10-iodo-1,2-dicarba-3-cobalta-closo-dodecaborane)-(10'-iodo-1',2'-dicarba-3'-cobalta-closo-dodecaborane) (16) were established by X-ray analysis of single crystals. 相似文献