55324-02-2Relevant articles and documents
Intramolecular Pd-catalyzed reductive amination of enolizable sp3-C-H bonds
Ford, Russell L.,Alt, Isabel,Jana, Navendu,Driver, Tom G.
supporting information, p. 8827 - 8831 (2019/10/28)
A palladium-catalyzed reductive cyclization of nitroarenes has been designed to construct sp3-C-NHAr bonds from sp3-C-H bonds by using an enolizable nucleophile to intercept a nitrosoarene intermediate. Exposure of ortho-substituted nitroarenes to 5 mol ?% of Pd(OAc)2 and 10 mol ?% of phenanthroline under 2 atm of CO constructs partially saturated 5-, 6-, or 7-membered N-heterocycles using α-pyridyl carboxylates, malonates, 1,3-dimethylbarbituric acid, 1,3-diones, or difurans as the nucleophile.
Synthesis of Aryl-Substituted 3,3a,4,5-Tetrahydropyrrolo[1,2- A [ quinolin-1(2 H)-ones and 2,3,4,4a,5,6-Hexahydro-1 H-pyrido[1,2- A [quinolin-1-ones
Watts, Field M.,Bunce, Richard A.
, p. 564 - 572 (2019/01/10)
A new route to the title benzo-fused angular tricyclic amides 3,3a,4,5-tetrahydropyrrolo- A nd 2,3,4,4a,5,6-hexahydro-1 H-pyrido[1,2- A [quinolin-1-ones is reported from 1-(tert-butyl) 6-ethyl 3-oxohexanedioate and 1-(tert-butyl) 7-ethyl 3-oxoheptanedioate. Alkylation of these β-keto diesters with a series of 2-nitrobenzyl bromides followed by acid hydrolysis and decarboxylation gives ethyl 6-(2-nitrophenyl)-4-oxohexanoates and ethyl 7-(2-nitrophenyl)-5-oxoheptanoates, respectively. Reductive amination under hydrogenation conditions followed by ester hydrolysis and condensative ring closure affords the final lactam products. The reactions proceed cleanly and only two chromatographic purifications are required.
Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations
Ju, Yeming,Miao, Di,Yu, Ruiyang,Koo, Sangho
, p. 2588 - 2599 (2015/04/21)
One pot syntheses of furan, thiophene, and pyrrole were accomplished by oxidative deacetylation using Mn(iii)/Co(ii) catalysts and the Paal-Knorr reaction from 1,5-dicarbonyl compounds, which are prepared from the conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds. The oxidative deacetylation and reductive cyclization of β-ketoesters derived from ethyl acetoacetate and o-nitrobenzyl bromides efficiently produced diversely substituted indoles. This journal is
Rh2(II)-catalyzed selective aminomethylene migration from styryl azides
Kong, Chen,Jana, Navendu,Driver, Tom G.
supporting information, p. 824 - 827 (2013/03/29)
Rh2(II)-Carboxylate complexes were discovered to promote the selective migration of aminomethylenes in β,β-disubstituted styryl azides to form 2,3-disubstituted indoles. Mechanistic data are also presented that suggest that the migration occurs stepwise before diffusion of the iminium ion.
A general strategy for the synthesis of cyclic N-aryl hydroxamic acids via partial nitro group reduction
McAllister, Laura A.,Bechle, Bruce M.,Dounay, Amy B.,Evrard, Edelweiss,Gan, Xinmin,Ghosh, Somraj,Kim, Ji-Young,Parikh, Vinod D.,Tuttle, Jamison B.,Verhoest, Patrick R.
experimental part, p. 3484 - 3497 (2011/06/24)
We describe a generalized approach to stereocontrolled synthesis of substituted cyclic hydroxamic acids (3-amino-1-hydroxy-3,4-dihydroquinolinones) by selective reduction of substituted 2-nitrophenylalanine substrates. Compounds in this series have antibacterial properties and have also recently been reported as KAT II inhibitors. The key nitrophenyl alanine intermediates are prepared enantioselectively in excellent yield by phase transfer catalyzed alkylation of the corresponding nitrobenzyl bromides. The scope and limitations of the reductive cyclization transformation have been explored with attention to the effects of substitution pattern and electronics on reaction efficiency and byproduct formation. In addition, a novel activated trifluoroethyl ester cyclization strategy has been developed as an alternate approach to the most sterically demanding systems in this series.
PHENYLALKYL AND PYRIDYLALKYL PIPERAZINE DERIVATIVES
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Page 63-64, (2010/02/07)
This invention relates to compounds of the formula (1) wherein R1, R3, R4, X1, and X2 are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system and other disorders.
