- Catalytic Strategy for Regioselective Arylethylamine Synthesis
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A mild, modular, and practical catalytic system for the synthesis of the highly privileged phenethylamine pharmacophore is reported. Using a unique combination of organic catalysts to promote the transfer of electrons and hydrogen atoms, this system performs direct hydroarylation of vinyl amine derivatives with a wide range of aryl halides (including aryl chlorides). This general and highly chemoselective protocol delivers a broad range of arylethylamine products with complete regiocontrol. The utility of this process is highlighted by its scalability and the modular synthesis of an array of bioactive small molecules.
- Boyington, Allyson J.,Seath, Ciaran P.,Zearfoss, Avery M.,Xu, Zihao,Jui, Nathan T.
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supporting information
p. 4147 - 4153
(2019/03/07)
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- Synthetic method for tyramine hydrochloride
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The invention discloses a synthetic method for tyramine hydrochloride. The synthetic method includes the steps that phenol is used as a raw material and reacts with aminoacetonitrile to generate p-hydroxy phenylaminoethanol, p-hydroxy phenylaminoethanol is subjected to catalytic reduction to obtain tyramine hydrochloride, activated carbon and copper powder are used as a composite catalyst, and the mass ratio of the activated carbon to the copper powder is (3-5):1. As the activated carbon and copper powder composite catalyst is added, the ratio of the dosage of the catalyst to the substrate weight can be reduced to (0.1-0.2):1. The catalytic efficiency is improved remarkably, the number of times of continuously using the catalyst can be increased to be 10 or more, the total yield of the reactions is increased, and the synthetic method has high economic benefits.
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Paragraph 0030; 0033; 0034
(2017/01/31)
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- Rapid Conventional and Microwave-Assisted Decarboxylation of L-Histidine and Other Amino Acids via Organocatalysis with R-Carvone under Superheated Conditions
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This article reports a new methodology taking advantage of superheated chemistry via either microwave or conventional heating for the facile decarboxylation of alpha amino acids using the recoverable organocatalyst, R-carvone. The decarboxylation of amino acids is an important synthetic route to biologically active amines, and traditional methods of amino acid decarboxylation are time consuming (taking up to several days in the case of L-histidine), are narrow in scope, and make use of toxic catalysts. Decarboxylations of amino acids including L-histidine occur in just minutes while replacing toxic catalysts with green catalyst, spearmint oil. Yields are comparable to or exceed previous methods and purification of product ammonium chloride salts is aided by an isomerization reaction of residual catalyst to phenolic carvacrol. The method has been shown to be effective for the decarboxylations of a range of natural, synthetic, and protected amino acids.
- Jackson, Douglas M.,Ashley, Robert L.,Brownfield, Callan B.,Morrison, Daniel R.,Morrison, Richard W.
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p. 2691 - 2700
(2015/12/18)
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- METHOD FOR DECARBOXYLATION OF AMINO ACIDS VIA IMINE FORMATION
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The present application provides methods for decarboxylation of amino acids via imine formation with a catalyst under superheated conditions in either a microwave or oil bath.
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Page/Page column 0045; 0056; 0066; 0067
(2014/09/30)
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- The first total synthesis of aplysamine 6, an inhibitor of isoprenylcysteine carboxy methyltransferase
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The first total synthesis of aplysamine 6, an inhibitor of isoprenylcysteine carboxy methyltransferase (Icmt), was accomplished in an overall high yielding reaction sequence.
- Ullah, Nisar,Arafeh, Khaled M.
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scheme or table
p. 158 - 160
(2009/04/14)
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- Thyronamine derivatives and analogs and methods of use thereof
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Thyronamine derivatives and analogs, methods of using such compounds, and pharmaceutical compositions containing them are disclosed. Methods of preparing such compounds are also disclosed
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- Phenethylamines via Heck Arylation of a New Vinylamine Equivalent
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A new vinylamine equivalent, N-vinyloxazolone 3, has been prepared in three steps and shown to undergo Heck arylation with a variety of substrates.The Heck adducts thus obtained are then converted in one step and high yield to phenethylamine hydrochlorides.As a general synthetic method for preparation of substituted phenethylamines, use of this new reagent is shown to be superior to N-vinylphthalimide in number of steps, regiospecificity, and chemical yield.
- Busacca, Carl A.,Johnson, Robert E.,Swestock, John
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p. 3299 - 3303
(2007/10/02)
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- Process for the preparation of arylethylamines and substituted arylethylamines
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This invention provides a process for directly preparing arylethylamines and their salts from (α-halo-α-oximino)acetophenones. The process involves hydrogenation in presence of a transition metal catalyst. The process is illustrated by conversion of 4-hydroxy-(α-chloro-α-oximino)acetophenone to Tyramine hydrochloride: STR1
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- Process for the preparation of arylalkylamines and substituted arylalkylamines
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Arylalkylamines (as the hydrochloride salt), e.g. tyramine hydrochloride, are prepared by hydrogenating substituted or unsubstituted aryl-α-oximinoalkyl ketones, e.g. p-hydroxyisonitroacetophenone, in either in an aqueous reaction medium comprising hydrochloric acid, essentially without the presence of a lower alkyl alcohol in said reaction medium, or in an aqueous reaction medium comprising water, hydrochloric acid, and a lower alkyl alcohol, wherein the alcohol comprises less than about 90% by volume of the reaction medium. A substituent on the aryl portion of the aryl-α-oximinoalkyl ketone must be on a position which activates the aromatic ring.
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- UN NOUVEL HETEROSIDE NITRE EXTRAIT D'ANNONA SQUAMOSA
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A new glycoside was isolated from a 60percent methanol extract of dried leaves and stems of Annona squamosa.Its chemical structure was determined as 4-(-2-nitroethyl)-1-benzene.Key Word Index -- Annona squamosa; Annonaceae; primeveroside; 4-(-2-nitroethyl)phenol; 4-(-2-aminoethyl)phenol; tyramine.
- Forgacs, P.,Desconclois, J. F.,Provost, J.,Tiberghien, R.,Touche, A.
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p. 1251 - 1252
(2007/10/02)
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