39716-23-9Relevant academic research and scientific papers
High-performance hypoiodite/hydrogen peroxide catalytic system for the oxylactonization of aliphatic γ-oxocarboxylic acids
Uyanik, Muhammet,Suzuki, Daisuke,Watanabe, Mizu,Tanaka, Hiroyasu,Furukawa, Kikuo,Ishihara, Kazuaki
supporting information, p. 387 - 389 (2015/03/30)
Highly efficient hypoiodite-catalyzed oxylactonization of aliphatic γ-oxocarboxylic acids to the corresponding γ-acyl-γ-butyrolactones was developed. Highly dilute reaction conditions and slow addition of the oxidant are both highly effective for promotin
TETRAHYDROINDOLE DERIVATIVES AS NADPH OXIDASE INHIBITORS
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Page/Page column 48, (2008/12/04)
The present invention is related to tetrahydroindolederivatives of Formula (I), pharmaceutical composition thereof, methods of preparation thereofand to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphateoxidase (NADPH Oxidase).
Solid-phase synthesis of decalin scaffolds by Robinson annulation with immobilised Nazarov reagents
Roettger, Svenja,Waldmann, Herbert
, p. 2093 - 2099 (2007/10/03)
A method for the synthesis of natural product-inspired decalin systems on solid support is reported. It employs the Robinson annulation as key step and immobilised Nazarov reagents as key intermediates. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Formation of aromatic rings through enamine annulation
Wang, Chen,Kohn, Harold
, p. 1773 - 1775 (2007/10/03)
(matrix presented) Condensation of pyrrolidine enamine of ketones with 1,4-diacetoxy-2-butanone provides a new, concise synthetic route to substituted benzenes, dihydroindenes, tetrahydronaphthalenes, and di- and octahydrophenanthrenes. The reaction produced modest yields with regiocontrol of the secondary amine substituent.
Addition Reactions of (Phenylsulfonyl)propadiene with 1-Pyrrolidinyl Enamines of Cyclic Ketones: Syntheses and Reactions of 1,3-Dienes Possessing an Allyl Sulfone Moiety
Hayakawa, Kenji,Takewaki, Makoto,Fujimoto, Ichiro,Kanematsu, Ken
, p. 5100 - 5105 (2007/10/02)
Addition reactions of (phenylsulfonyl)propadiene (1) with various 1-pyrrolidinyl enamines have been investigated.Allene 1 and enamines of cyclic ketones (2, 7-14) readily underwent the Michael-type addition reactions at -50 deg C to give the adducts 3, 15-20, and/or their isomers 4 and 21-26, which apparently arose by base-catalyzed isomerization of the former.These adducts were conveniently converted into the corresponding 1,3-dienes possessing allyl sulfone moiety (28, 38-45) through allyl acetates (27, 30-37) by base-promoted (n-BuLi, -50 deg C) 1,4-elimination of acetic acid to vinyl sulfones followed by deconjugation to allyl sulfones.The synthetic versatility of these dienes was revealed by the Diels-Alder reactions with dimethyl acetylenedicarboxylate (DMAD) and alkylation reactions via α-sulfonyl carbanions.
Stereoselective Reductions of Substituted Cyclohexyl and Cyclopentyl Carbon-Nitrogen ? Systems with Hydride Reagents
Hutchins, Robert O.,Su, Wei-Yang,Sivakumar, Ramachandran,Cistone, Frank,Stercho, Yuriy P.
, p. 3412 - 3422 (2007/10/02)
Reductions of 3- and 4-substituted cyclohexyl imines, iminium salts, and enamines (via iminium ions) with various hydride reagents reveal that while small reagents (NaBH4, NaBH3CN) favor axial approach as observed with the corresponding ketones, even moderately bulky reagents (i.e., acetoxyboranes) attack preferentially from the equatorial side.This is in direct contrast to the results observed for the same reagents with the corresponding ketones and is interpreted as implying that additional steric interactions induced by the nitrogen substituents encumber axial attack by substituted hydride reagents and force approach from the equatorial direction.The very bulky tri-sec-butylborohydride anion affords highly stereodiscriminating equatorial attack.Reductions of 2-alkylcyclohexyl and 2-alkylcyclopentyl imines and enamines also proceed with high stereoselectivity to give cis-2-alkyl cyclic amines with both hindered and unhindered reagents.This is interpreted to be the result of (1) augmented steric interactions between nitrogen substituents and equatorial 2-alkyl groups (1,3-allylic strain) which induces conformational changes to favor the axial 2-alkyl conformer and (2) hindrance toward equatorial approach by reagents induced by axial alkyl substituents.The result is that equatorial approach is favored with equatorial 2-alkyl conformers and preferential axial approach with axial 2-alkyl conformers, leading to stereoselective production of cis-2-alkylamines. trans-2-n-Propyl-4-tert-butylcyclohexanone is reduced by LiBH(sec-Bu)3 preferentially from the axial direction in contrast to the usual highly selective equatorial attack observed with other cyclohexanones.
ENAMINE CHEMISTRY XX. SYNTHESIS OF FURAN DERIVATIVES BY REDUCTIVE CYCLISATION OF ENAMINES
Carlsson, S.,El-Barbary, A. A.,Lawesson, S.-O.
, p. 643 - 650 (2007/10/02)
Enamines, I, prepared from cyclohexanones or cyclopentanones and pyrrolidine are alkylated with 2-bromoesters (ethyl 2-bromoethanoate, ethyl 2-bromopropanoate, methyl 2-bromopropanoate) to give new enamines, II, which after treatment with LiAlH4 undergo reductive cyclisation reactions giving the furan derivatives, III (7a-pyrrolidino-octahydrobenzofurans, 6a-pyrrolidino-hexahydrocyclopentafurans) in almost quantitative yields.The compounds III are hydrolyzed with hydrochloric acid to octahydrobenzofuran-7a-ols or hexahydrocyclopentafuran-6a-ols, IV.Elimination of pyrrolidine from III with oxalic acid in anhydrous dioxane yields condensed dihydrofurans, V.
1,2-Diphenyl-4,5,6,7-tetrahydroindoles
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, (2008/06/13)
This invention relates to novel 1-[4-(R1 R2 N-Cn H2n -O)phenyl]-5-R4 -2-(4-R3 -phenyl)indoles having antifertility and hypocholesterolemic activities and to novel intermediates for their preparation.
3-Hydrazino-cycloalkyl[c]pyridazines
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, (2008/06/13)
This invention provides aminopyridazine derivatives of formula I, SPC1 wherein R1 is amino, or an EQU1 group, wherein each of R3 and R4 is alkyl of 1 to 4 carbon atoms, or R3 and R4 together with the carbon atom to which they are bound, form a cycloalkylidene radical of 5 to 12 carbon atoms, R2 is hydrogen or methyl, A is a --(CH2)n -- group, Wherein n is 0 or an integer from 1 to 7, or an >N--CO--R5 group, Wherein R5 is alkyl or alkenyl of 1 to 16 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, 1-adamantyl, or a --(CH2)m --R6 group, Wherein m is 0 or an integer from 1 to 4, and R6 is phenyl; phenyl monosubstituted by fluorine, chlorine, bromine, alkyl or alkoxy of 1 to 4 carbon atoms, alkylmercapto of 1 to 4 carbon atoms, or phenyl; phenyl substituted by two or three substituents of the group chlorine, alkyl or alkoxy of 1 to 4 carbon atoms; diphenylmethyl, the phenyl rings of which may be monosubstituted by fluorine, chlorine, bromine, alkyl or alkoxy of 1 to 4 carbon atoms; or naphthyl, Or an --OR7 group, Wherein R7 is alkyl or alkenyl of 1 to 4 carbon atoms, or phenyl, phenylalkyl or phenylalkenyl which may be monosubstituted on the phenyl ring by chlorine, alkyl or alkoxy of 1 to 4 carbon atoms, and in which the alkylene or alkenylene chain is of 1 to 4 carbon atoms, And R8 and R9 are each hydrogen or alkyl of 1 to 4 carbon atoms, And acid addition salts thereof. The invention also provides processes for the production of said compounds. Said compounds and pharmaceutically acceptable acid addition salts thereof are useful as antihypertensive agents.
