7623-19-0Relevant academic research and scientific papers
Synthesis and dopamine receptor pharmacological evaluations on ring C ortho halogenated 1-phenylbenzazepines
Alberts, Ian,Giri, Rajan,Harding, Wayne W.,Namballa, Hari K.,Sarker, Ananta
supporting information, (2020/06/19)
A series of 1-phenylbenzazepines containing bromine or chlorine substituents at the ortho position of the appended phenyl ring (2′-monosubstituted or 2′,6′- disubstituted patterns) were synthesized and evaluated for affinity towards dopamine D1
Mononuclear Nonheme Iron(III)-Iodosylarene and High-Valent Iron-Oxo Complexes in Olefin Epoxidation Reactions
Wang, Bin,Lee, Yong-Min,Seo, Mi Sook,Nam, Wonwoo
supporting information, p. 11740 - 11744 (2015/10/05)
High-spin iron(III)-iodosylarene complexes are highly reactive in the epoxidation of olefins, in which epoxides are formed as the major products with high stereospecificity and enantioselectivity. The reactivity of the iron(III)-iodosylarene intermediates is much greater than that of the corresponding iron(IV)-oxo complex in these reactions. The iron(III)-iodosylarene species - not high-valent iron(IV)-oxo and iron(V)-oxo species - are also shown to be the active oxidants in catalytic olefin epoxidation reactions. The present results are discussed in light of the long-standing controversy on the one oxidant versus multiple oxidants hypothesis in oxidation reactions. On active duty: High-spin iron(III)-iodosylarene complexes epoxidize olefins with high stereospecificity and enantioselectivity. The iron(III)-iodosylarene species, not high-valent iron(IV)- and iron(V)-oxo species, are the active oxidants in catalytic olefin epoxidation reactions. The present results resolve the long-standing controversy on the one oxidant versus multiple oxidants hypothesis in oxidation reactions.
S-Methylidene agents: preparation of chiral non-racemic heterocycles
Forbes, David C.,Bettigeri, Sampada V.,Patrawala, Samit A.,Pischek, Susanna C.,Standen, Michael C.
supporting information; experimental part, p. 70 - 76 (2009/04/06)
Reaction of sulfur ylide with aldehyde, imine, and ketone functionality affords the desired three-membered heterocycle in excellent yield. The sulfur ylide is generated in situ upon decarboxylation of carboxymethylsulfonium betaine functionality. Of the seven carboxymethylsulfonium betaine derivatives surveyed, the highest level of conversion of π-acceptor to heterocycle was obtained with the one having S-methyl and S-phenyl functionality bound to a thioacetate derivative. Methylene aziridinations and epoxidations involving the decarboxylation of carboxymethylsulfonium betaine functionality complements existing technologies with the advantages of the reaction protocol, levels of conversion, and scope. While moderate levels of diastereocontrol were observed in the aziridination of imine functionality, the four oxiranes resolved using Jacobsen's Co(II)-salen complex were obtained in both high yield and enantioselectivity. The isolated chiral non-racemic oxiranes constitute the formal synthesis of chelonin B and combretastatin starting from 3-bromo-4-methoxybenzaldehyde and 3,4,5-trimethoxybenzaldehyde, respectively.
Aryl-substituted sulfonium betaines: Preparation and use in the epoxidation of aldehydes
Forbes, David C.,Amin, Sejal R.,Bean, Christie J.,Standen, Michael C.
, p. 8287 - 8290 (2007/10/03)
Thermally induced decarboxylation of carboxymethylsulfonium betaines results in formation of the corresponding sulfur ylides in situ. Decarboxylation rates for a range of arylcarboxymethylsulfonium betaine salts have been determined using NMR spectroscopy, and the efficiency of ylide generation and trapping has been evaluated via methylidene transfer to a range of aldehydes to form epoxides.
Sulfur ylides via decarboxylation of carboxymethylsulfonium betaines: A novel and mild protocol for the preparation of oxiranes
Forbes, David C.,Standen, Michael C.,Lewis, Derrick L.
, p. 2283 - 2286 (2007/10/03)
(Matrix presented) A novel protocol for the generation of sulfur ylides is described. The overall process involves thermal decarboxylation of a carboxymethyl-sulfonium betaine to give a sulfur ylide that, in the presence of an aldehyde, affords the corresponding terminal oxirane. Yields were found to correlate with the electron deficiency of the aryl aldehyde. In situ generation of betaine in the presence of an aldehyde successfully afforded the desired oxirane in moderate yield, thus demonstrating the feasibility of a catalytic process.
N-hydroxyalkyl derivatives of 3β-phenyltropane and 1-methylspiro[1H- indoline-3,4'-piperidine]: Vesamicol analogues with affinity for monoamine transporters
Efange, Simon M. N.,Kamath, Ashok P.,Khare, Anil B.,Kung, Mei-Ping,Mach, Robert H.,Parsons, Stanley M.
, p. 3905 - 3914 (2007/10/03)
As part of our ongoing structure-activity studies of the vesicular acetylcholine transporter ligand 2-(4-phenylpiperidino)cyclohexanol [vesamicol, 1), 22 N-hydroxy(phenyl)alkyl derivatives of 3β-phenyltropane, 6, and 1-methylspiro[1H-indoline-3,4'-piperidine], 7, were synthesized and tested for binding in vitro. Although a few compounds displayed moderately high affinity for the vesicular acetylcholine transporter, no compound was more potent than the prototypical vesicular acetylcholine transporter ligand vesamicol. However, a few derivatives of 6 displayed higher affinity for the dopamine transporter than cocaine. We conclude that modification of the piperidyl fragment of 1 will not lead to more potent vesicular acetylcholine transporter ligands.
Dihydroimidazoles in Synthesis: C-Alkylation of 1-Benzyl-2-(α-lithioalkyl)-4,5-dihydroimidazoles and a Synthesis of Alkanoic Acids
Anderson, Michael W.,Jones, Raymond C. F.,Saunders, John
, p. 205 - 210 (2007/10/02)
1-Benzyl-2-alkyl-4,5-dihydroimidazoles have been (laterally) metallated and C-alkylated by reaction with alkyl halides and an epoxide; intramolecular C-alkylation has led to a tetrahydro-5H-pyrroloimidazole.Hydrolysis of the 4,5-dihydroimidazoles to produce alkanoic acids completes a homologation sequence.
