Régiosélectivité d'additions de nucléophiles sur des dialkoxycarbonyle quinoxalinotropones

1983 ◽  
Vol 61 (8) ◽  
pp. 1806-1812 ◽  
Author(s):  
Alain Turck ◽  
Roland Boutte ◽  
Guy Quéguiner
Keyword(s):  
Sodium Methoxide ◽  
Carbon Nucleophiles ◽  
Ethyl Malonate ◽  
Nitrogen Nucleophiles ◽  
Substituted Hydrazines

We have studied the regioselectivity of Michael type additions on tropones attached to quinoxalines, i.e. dialkoxycarbonyl quinoxalinotropones. We used carbon nucleophiles (ethyl malonate and malononitrile), oxygen nucleophiles (sodium methoxide), sulphur nucleophiles (methyl and benzyl mercaptans), and nitrogen nucleophiles (methyl and phenylhydrazine, aniline). We have shown that, in general, these reactions lead to 1,4-monoadditions or to bridged products arising from a bis-1,4-addition process. We have determined the structures of the complexes obtained by comparison to the work of Fohlisch etal. in the homoaromatic series. For the case of substituted hydrazines, we present some evidence on the rearrangement mechanisms proposed by these authors. [Journal translation]

scholarly journals Steric and Polar Factors Affecting Heteroring Opening of 2-[2-carboxy-3,4,5,6-tetrachloro]phenyl-4H-3,1-Benzoxazin-4-one by Nitrogen and Carbon Nucleophiles

2009 ◽  
Vol 5 (2) ◽  
pp. 661-668
Author(s):  
Jehan Mahmoud Morsy ◽  
Maher Abdel Aziz El-Hashash
Keyword(s):  
Ring Opening ◽  
Reaction Conditions ◽  
Factors Affecting ◽  
Carbon Nucleophiles ◽  
Nitrogen Nucleophiles

The behavior of 2-[2-carboxy-3,4,5,6-tetrachloro]phenyl-4H-3,1-Benzoxazin-4-  one towards Nitrogen nucleophiles and Carbon nucleophiles under Friedel–Crafts' reaction conditions has been investigated and steric versus polar factors affecting ring opening has been studied.

scholarly journals Investigation and Synthesis of Some Novel Spiro Heterocycles Related to Indoline Moiety

2014 ◽  
Vol 6 (2) ◽  
pp. 293-307 ◽  
Author(s):  
Y. A. B. El-Ossaily ◽  
R. M. Zaki ◽  
S. A. Metwally
Keyword(s):  
Hydrogen Peroxide ◽  
Thioglycolic Acid ◽  
Magnesium Salt ◽  
The Novel ◽  
Spectral Analyses ◽  
Carbon Nucleophiles ◽  
Chemical Structures ◽  
Nitrogen Nucleophiles

Reactions of indole-2,3-dione 1 with 2-mercaptobenzimidazole, o-phenylenediamine, 2-aminophenol, 2-aminobenzothiazole, 2-aminobenzimidazole and 3-methyl-1-phenyl-2-pyrazolin-5-one were carried out to give compounds spiroindolethiazetobenzimidazole 2, spirobenzimidazole(oxazole)indoline 3a,b, benzothiazol(imidazol) iminoindolinone 4a,b and methyloxoindolylidenepyrazolone 5 respectively. Compound 5 was reacted with 2-aminophenol as well as o-phenylenediamine to give new spirooxazepine and diazepine derivatives 6a,b respectively. Reaction of 5 with nitrogen nucleophiles as well as carbon nucleophiles was investigated to furnish new spiro heterocycles 7-11. The reaction of 2-(2-oxo-1,2-dihydroindol-3-ylidene)malononitrile compound 12 with 3-methyl-1-phenyl-2-pyrazoline-5-one was carried out to give spiroindolopyranopyrazolo derivative 13. Compounds 4a,b was reacted with thioglycolic acid to give thiazolidinone derivatives 14a,b. Epoxidation of 5 using monoperoxyphthalic acid magnesium salt hexahydrate and hydrogen peroxide were executed to afford the novel dispiro (2-pyrazolin oxiraneindoline)dione compound 15. The chemical structures of the synthesized compounds were well established by elemental and spectral analyses.   Keywords: Spiroheterocycles; Epoxidation; Diazapines, Oxazepines; Spirothiazolidinone.  © 2014 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved.   doi: http://dx.doi.org/10.3329/jsr.v6i2.17590 J. Sci. Res. 6 (2), 303-317 (2014)

Immunocytochemical localization of desmin and vimentin in chick embryonic myocardial cells

1990 ◽  
Vol 48 (3) ◽  
pp. 448-449
Author(s):  
Yukiko Sugi
Keyword(s):  
Sodium Methoxide ◽  
Intermediate Filament Protein ◽  
Chick Embryos ◽  
Immunocytochemical Localization ◽  
Myocardial Cells ◽  
Immunofluorescence Study ◽  
Immunofluorescent Localization ◽  
Rabbit Igg ◽  
Semithin Sections ◽  
Filament Protein

In cultured skeletal muscle cells of chick, one intermediate filament protein, vimentin, is primarily formed and then synthesis of desmin follows. Coexistence of vimentin and desmin has been immunocytochemically confirmed in chick embryonic skeletal musclecells. Immunofluorescent localization of vimentin and desmin has been described in developing myocardial cells of hamster. However, initial localization of desmin and vimentin in early embryonic heart has not been reported in detail. By quick-freeze deep-etch method a loose network of intermediate filaments was revealed to exist surrounding myofibrils. In this report, immunocytochemical localization of desmin and vimentin is visualized in early stages of chick embryonic my ocardium.Chick embryos, Hamburger-Hamilton (H-H) stage 8 to hatch, and 1 day old postnatal chicks were used in this study. For immunofluorescence study, each embryo was fixed with 4% paraformaldehyde and embedded in Epon 812. De-epoxinized with sodium methoxide, semithin sections were stained with primary antibodies (rabbit anti-desmin antibody and anti-vimentin antibody)and secondary antibody (RITC conjugated goat-anti rabbit IgG).

Synthesis of Allenyl Ketones by the Palladium-Catalyzed Carbonylation of 2-Alkynyl Carbonates in the Presence of Soft Carbon Nucleophiles

Synlett ◽  
1991 ◽  
Vol 1991 (09) ◽  
pp. 697-698 ◽  
Author(s):  
Tadakatsu Mandai ◽  
Hiroaki Kunitomi ◽  
Kiyoto Higashi ◽  
Mikio Kawada ◽  
Jiro Tsuji
Keyword(s):  
Carbon Nucleophiles ◽  
Palladium Catalyzed ◽  
Soft Carbon

Nickel-Catalyzed Regioselective Hydroalkylation of 1,3-Dienes with Hydrazones

2019 ◽  
Author(s):  
Leiyang Lv ◽  
Dianhu Zhu ◽  
Zihang Qiu ◽  
Jianbin Li ◽  
Chao-Jun Li
Keyword(s):  
Catalytic Method ◽  
Unsaturated Hydrocarbons ◽  
Carbon Nucleophiles ◽  
Aryl Aldehydes ◽  
Aldehydes And Ketones ◽  
Sterically Hindered

Hydroalkylation of unsaturated hydrocarbons with unstablized carbon nucleophiles is difficult and remains a major challenge. The disclosed examples so far mainly focused on the involvement of heteroatom and/or stabilized carbon nucleophiles as efficient reaction partners. Reported here is an unprecedented regioselective nickel-catalyzed hydroalkylation of 1,3-dienes with hydrazones, generated in situ from abundant aryl aldehydes and ketones and acted as both the sources of unstabilized carbanions and hydride. With this strategy, both terminal and sterically hindered internal dienes are hydroalkylated efficiently in a highly selective manner, thus providing a novel and reliable catalytic method to construct challenging C(sp3)-C(sp3) bonds.

Reaction of 1,4-dibromohexafluoro-2-butene with O- and N-nucleophiles

1988 ◽  
Vol 53 (3) ◽  
pp. 619-625 ◽  
Author(s):  
Ivan Hemer ◽  
Věra Moravcová ◽  
Václav Dědek
Keyword(s):  
Kinetic Study ◽  
Sodium Methoxide ◽  
Allylic Rearrangement ◽  
Rearrangement Product

Reaction of 1,4-dibromohexafluoro-2-butene (I) with sodium methoxide, ethoxide or isopropoxide in the corresponding alcohols proceeds with allylic rearrangement under formation of 3-alkoxy-4-bromohexafluoro-1-butenes II-IV. A kinetic study has proven the SN2’ mechanism for reaction of I with potassium phenoxide leading to 4-bromo-3-phenoxyhexafluoro-1-butene (V). Also the reaction of I with ammonia, affording 3-amino-4-bromo-2,4,4-trifluoro-2-butenenitrile (IX), is compatible with the allylic rearrangement by SN2’ mechanism. On the contrary, reaction of I with diethylamine gave no rearrangement product and, after hydrolysis, afforded N,N-diethyl-4-bromo-2,3,3,4,4-pentafluorobutanamide (XVI) and N,N-diethyl-4-bromo-2,3,4,4-tetrafluoro-2-butenamide (XVII) in the ratio 85:15.

Reactions of 3-cyano-1-methylquinolinium methyl sulphate with some C-acids and with p-nitroaniline

1981 ◽  
Vol 46 (2) ◽  
pp. 503-505 ◽  
Author(s):  
Oldřich Kocián ◽  
Miloslav Ferles
Keyword(s):  
Sodium Methoxide ◽  
Ethyl Cyanoacetate ◽  
Derivatives Of

The action of malononitrile, ethyl cyanoacetate, dibenzoylmethane and/or p-nitroaniline on compound I in the presence of sodium methoxide gives rise to derivatives of 3-cyano-1-methyl-1,4-dihydroquinoline, II and III

Kinetic salt effects in the hydrolysis of ethyl malonate, methyl glutarate and ethyl adipate semiesters

1986 ◽  
Vol 51 (12) ◽  
pp. 2781-2785 ◽  
Author(s):  
M. Martín Herrera ◽  
J. J. Maraver Puig ◽  
F. Sánchez Burgos
Keyword(s):  
Salt Effect ◽  
Alkaline Media ◽  
Salt Effects ◽  
Coulombic Interaction ◽  
Hydroxide Ion ◽  
Ethyl Malonate ◽  
Hydrolysis Of

A study is made on the kinetic salt effect on the reaction of hydrolysis of several charged esters in alkaline media. The results are interpreted on the basis of the coulombic interaction, the salting in of hydroxide ion and a third component depending on size of the substrate.

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