Organophosphorus compounds. XI. Synthesis of some 1,2,3,4,5,6-Hexahydro-1,5-methano-4,1-benzazaphosphocines

1974 ◽  
Vol 27 (4) ◽  
pp. 815 ◽  
Author(s):  
DJ Collins ◽  
LE Rowley ◽  
JM Swan
Keyword(s):  
Analgesic Activity ◽  
Acid Chloride ◽  
Organophosphorus Compounds ◽  
Mild Conditions ◽  
Tricyclic Compounds ◽  
Vinyl Group ◽  
Successive Reduction

1-Hydroxy-1,2,3,4-tetrahydrophosphinoline 1-oxide (2a) was converted via the corresponding acid chloride (2b) into the 1-vinylphosphine oxide (3) which underwent a Michael-like addition with dimethylamine to give 1-(2'-dimethylaminoethyl)-1,2,3,4-tetrahydrophosphinoline 1-oxide (6). The successive reduction of (6) with trichlorosilane, and oxidation with sulphur afforded the phosphine sulphide (7). The reaction of 1-vinyl-1,2,3,4-tetrahydrophosphinoline 1-oxide (3) with N-bromosuccinimide followed by treatment with dimethylformamide gave 1-vinyl-1,2-dihydrophosphinoline 1-oxide which, under mild conditions, underwent Michael-like addition of amines to the vinyl group to give, for example, 1-(2'-propylaminoethy1)-1,2-dihydrophosphinoline 1-oxide. When heated in a sealed tube at 140-150° in water for 60 h this amine was converted into 4-propyl-1,2,3,4,5,6-hexa- hydro-1,5-methano-4,1-benzazaphosphocine 1-oxide. Several related tricyclic compounds including the corresponding phosphines and phosphine sulphides were synthesized. Several of the new aminophosphorus compounds were tested for analgesic activity.

Organophosphorus compounds. XVI. 2-(N-Dialkylamino)alkyldiphenylphosphines, phosphine oxides and sulphides as analogues of methadone

1974 ◽  
Vol 27 (11) ◽  
pp. 2365 ◽  
Author(s):  
DJ Collins ◽  
S Mollard ◽  
N Rose ◽  
JM Swan
Keyword(s):  
Analgesic Activity ◽  
Secondary Amine ◽  
Organophosphorus Compounds ◽  
Phosphine Oxides ◽  
Reaction Conditions ◽  
Diphenylvinylphosphine Oxide

A series of 2-(N-dialkylamino)ethyldiphenylphosphine oxides and sulphides was prepared by the addition of a secondary amine to diphenylvinylphosphine oxide, or the phosphine sulphide, respectively. Similarly, a series of 2-(N-dialkylamino)propyldiphenylphosphine oxides was prepared from diphenylprop-1-enylphosphine oxide, or from diphenylprop-2-enylphosphine oxide which isomerized under the reaction conditions. Reduction of the 2-(N-dialkylamino)propyldiphenylphosphine oxides with trichlorosilane, and oxidation of the phosphines with sulphur, afforded the corresponding phosphine sulphides. ��� None of the compounds showed significant analgesic activity.

Organophosphorus compounds with anti-inflammatory and analgesic activity (review)

1993 ◽  
Vol 26 (7-8) ◽  
pp. 565-575 ◽  
Author(s):  
V. Kh. Syundyukova ◽  
E. G. Neganova ◽  
B. K. Beznosko ◽  
E. N. Tsvetkov
Keyword(s):  
Analgesic Activity ◽  
Organophosphorus Compounds ◽  
Anti Inflammatory

Reactions of Ethylene with Rhodium (III) Chloride. Part III. The Catalytic Oxidation of Ethylene to Acetaldehyde in Aqueous Hydrochloric Acid Solutions Containing Pentachloroaquorhodate(III)

1972 ◽  
Vol 50 (11) ◽  
pp. 1698-1707 ◽  
Author(s):  
B. R. James ◽  
M. Kastner
Keyword(s):  
Hydrochloric Acid ◽  
Acid Chloride ◽  
Rate Constants ◽  
Acid Solutions ◽  
Reaction Conditions ◽  
Gas Uptake ◽  
Mild Conditions ◽  
Aqueous Acid ◽  
Hydrochloric Acid Solutions ◽  
Kinetics Of

In the presence of iron(III) or other oxidants, aqueous acid chloride solutions of RhCl5(H2O)2− catalyze under mild conditions the oxidation of ethylene to acetaldehyde. The kinetics of the reaction measured by gas-uptake techniques indicate the presence of both ethylene dependent and independent paths. Besides fully protonated anions, hydroxy species such as RhCl5 (OH)3− and RhCl4(OH)(H2O)2−, although present in very small concentrations, are significantly reactive towards ethylene. A mechanism, based on that postulated for a similar palladium(II) system in the well-known Wacker process, is presented. Under our reaction conditions the slow steps in the rhodium system involve formation of π-complexes in the ethylene dependent paths and the formation of tetrachlororhodate(III) complexes in the ethylene independent paths. Iron(III) regenerates the rhodium(III) catalyst by oxidation of the rhodium(I). Rate constants are estimated for the various reaction paths.

Ene-thiol reaction of C3-vinylated chlorophyll derivatives in the presence of oxygen: synthesis of C3-formyl-chlorins under mild conditions

2013 ◽  
Vol 17 (12) ◽  
pp. 1188-1195 ◽  
Author(s):  
Takanori Fukusumi ◽  
Natsuki Takei ◽  
Yubi Tateno ◽  
Takuya Aoki ◽  
Ai Ando ◽  
...  
Keyword(s):  
Metal Catalyst ◽  
Central Metal Atom ◽  
Central Metal ◽  
Formyl Group ◽  
Mild Conditions ◽  
Thiol Reaction ◽  
Regioselective Oxidation ◽  
A Minor ◽  
Vinyl Group ◽  
Chlorophyll Derivatives

Reactions of thiol with the C 3-vinyl group of various chlorophyll (Chl) derivatives were examined. The reactions resemble thiol-olefin co-oxidation, except that the vinyl C = C double bond was cleaved to afford a formyl group without any transition metal catalyst, and that the simple anti-Markovnikov adduct of thiol to olefin was obtained as a minor product. Peripheral substituents of Chl derivatives little affected the reaction, while the central metal atom of the chlorin macrocycle influenced the composition of the products. Oxygen and acid dissolved in the reaction mixture can facilitate the oxidation. Sufficiently mild conditions in this regioselective oxidation at the C 31-position are significant in bioorganic chemistry.

Opportunities and challenges for combining electro- and organometallic catalysis in C(sp2)-H phosphonation

2019 ◽  
Vol 91 (1) ◽  
pp. 17-31 ◽  
Author(s):  
Yulia H. Budnikova
Keyword(s):  
Closed System ◽  
Atmospheric Pressure ◽  
Room Temperature ◽  
Organophosphorus Compounds ◽  
Reaction System ◽  
Historical Background ◽  
Aromatic Carbon ◽  
Low Concentration ◽  
Mild Conditions ◽  
Unconventional Methods

AbstractThe chemistry of organoelemental compounds including carbon-phosphorus derivatives is now one of the most rapidly developing fields of research, regarding both fundamental science and solution of applied problems. Extensive opportunities for the synthesis of organophosphorus compounds are opened up by the use of unconventional methods, first of all, electrochemical ones, which combine the benefits of usual homogeneous chemistry in solution and electrochemistry, where reactants are generated at the electrodes directly in the reaction system. The interest in the organic electrosynthesis is caused by several factors, including mild conditions (room temperature, atmospheric pressure), the possibility of conducting reactions in a closed system with a low concentration of the catalyst, which is readily regenerated. This mini-review generalizes the achievements in the field of development of new electrochemical, efficient and atom-economical, catalytic methods for the formation of aromatic carbon – phosphorus bonds and some historical background of these approaches.

scholarly journals Black Phosphorus: An Effective Feedstock for the Synthesis of Phosphorus-Based Chemicals

CCS Chemistry ◽  
2019 ◽  
Vol 1 (2) ◽  
pp. 166-172 ◽  
Author(s):  
Lie Wu ◽  
Shi Bian ◽  
Hao Huang ◽  
Jiahong Wang ◽  
Danni Liu ◽  
...  
Keyword(s):  
Organophosphorus Compounds ◽  
Black Phosphorus ◽  
White Phosphorus ◽  
The Novel ◽  
Phosphine Oxides ◽  
Elemental Phosphorus ◽  
One Pot ◽  
Mild Conditions ◽  
Novel Concept ◽  
Phosphine Sulfide

We propose and demonstrate the novel concept of synthesizing organophosphorus compounds directly from black phosphorus (BP) nanoparticles as the feedstock. Compounds such as alkyl phosphines, alkyl phosphine oxides, phosphine sulfide, and hexafluorophosphate anion are prepared with good isolation yields under mild conditions. Selective synthesis of primary, secondary, and tertiary organophosphorus compounds is also demonstrated utilizing this one-pot approach. Reaction mechanisms are proposed and discussed. Compared with traditional white phosphorus (P4)-based methods, the new synthetic concept and process utilizing elemental phosphorus are more efficient and environmentally friendly.

Anti-inflammatory and analgesic activity of Jateorhiza macrantha (Menispermaceae)

Planta Medica ◽  
2013 ◽  
Vol 79 (13) ◽  
Author(s):  
GO Ajayi ◽  
O Salako ◽  
IM Mosebolatan
Keyword(s):  
Analgesic Activity ◽  
Anti Inflammatory
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