137858-58-3Relevant academic research and scientific papers
Facile preparation of α-amino ketones from oxidative ring-opening of aziridines by pyridine N-oxide
Luo, Zhi-Bin,Wu, Jing-Yu,Hou, Xue-Long,Dai, Li-Xin
, p. 3428 - 3430 (2008/09/19)
The oxidative ring-opening reaction of a variety of activated aziridines by pyridine N-oxide provided α-amino ketones or α-amino aldehydes in good yields. The Royal Society of Chemistry.
Chemistry and biology of diazonamide A: Second total synthesis and biological investigations
Nicolaou,Hao, Junliang,Reddy, Mali V.,Rao, Paraselli Bheema,Rassias, Gerasimos,Snyder, Scott A.,Huang, Xianhai,Chen, David Y.-K.,Brenzovich, William E.,Giuseppone, Nicolas,Giannakakou, Paraskevi,O'Brate, Aurora
, p. 12897 - 12906 (2007/10/03)
As an especially unique target for chemical synthesis, diazonamide A has the potential to be constructed through a plethora of synthetic routes, each attended by different challenges and opportunities for discovery. In this article, we detail our second total synthesis of diazonamide A through a sequence entirely distinct from that employed in our first campaign, one whose success required the development of several special strategies and tactics. We also disclose our complete studies regarding the chemical biology of diazonamide A and its structural congeners, and more fully delineate the scope of our protocol for Robinson-Gabriel cyclodehydration using pyridine-buffered POCl 3.
Parallel synthesis of substituted imidazoles from 1,2-aminoalcohols
Bleicher, Konrad H.,Gerber, Fernand,Wüthrich, Yves,Alanine, Alexander,Capretta, Alfredo
, p. 7687 - 7690 (2007/10/03)
Substituted imidazoles can be prepared efficiently from cyclic or acyclic 1,2-aminoalcohols via a four-step procedure involving acylation of the amine, oxidation of the alcohol, imine formation and cyclization. Examples are presented and the methodology i
NITROGEN-CONTAINING CYCLOHETERO CYCLOALKYLAMINOARYL DERIVATIVES FOR CNS DISORDERS
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, (2008/06/13)
Certain nitrogen-containing cyclohetero cycloalkylaminoaryl compounds are described for treatment of CNS disorders such as cerebral ischemia, psychotic disorders, convulsions and parkinsonism. Compounds of particular interest are of the formula STR1 wherein R 1 is selected from hydrido, loweralkyl, cycloalkylalkyl of four to six carbon atoms and loweralkenylloweralkyl; wherein each of R 2 and R 3 is independently selected from hydrido and loweralkyl; wherein each of R 4 through R 7, R 10 and R 11 is independently selected from hydrido, hydroxy, loweralkyl, benzyl, phenoxy, benzyloxy and haloloweralkyl; wherein n is a number selected from four through six; wherein p is a number selected from zero through four; wherein q is a number selected from three through five; wherein A is selected from phenyl, naphthyl and thienyl; wherein any of the foregoing A groups can be further substituted with one or more substituents independently selected from hydrido, hydroxy, loweralkyl, loweralkoxy, halo, haloloweralkyl, amino, monoloweralkylamino and diloweralkylamino; or a pharmaceutically acceptable salt thereof.
Asymmetric reductive amination of cycloalkanones, XIII: Enantioselective amidoamination: A new regiospecific strategy for the synthesis of chiral cyclohexane-1,2-diamino-derivatives
Schlichter,Frahm
, p. 429 - 436 (2007/10/02)
Asymmetric synthesis of trans- and cis-2-Benzamido- or 2-Phenyl-acetamido-cyclohexane-amines 7 and 8 by means of reductive amination and hydrogenolysis is described. Condensation of the amido-ketones 3 with chiral auxiliary (R)-(+) and (S)-(-)-1-phenylethylamine, respectively, leads to the amido-imines 4, which are hydrogenated over Raney-Ni to yield simultaneously enantiomerically pure secondary trans- and cis-2-amido-cyclohexane-amines 5 and 6.
NOVEL, ENANTIOSELECTIVE SYNTHESIS OF VICINAL CYCLOHEXANE-DIAMINES AS KEY-INTERMEDIATES FOR HIGHLY SELECTIVE OPIOID KAPPA AND SIGMA AGONISTS.
Schlichter, Wolfgang H.,Frahm, August W.
, p. 329 - 332 (2007/10/02)
Enantiomers of Cyclohexane-1,2-diamines have been synthesized via two different synthetic approaches by asymmetric catalytic hydrogenation.
Nitrogen-containing cyclohetero cycloalkylaminoaryl derivatives for CNS disorders
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, (2008/06/13)
Certain nitrogen-containing cyclohetero cycloalkylaminoaryl compounds are described for treatment of CNS disorders such as cerebral ischemia, psychotic disorders and convulsions. Compounds of particular interest are of the formula STR1 wherein R1 is selected from hydrido, loweralkyl, cycloalkylalkyl of four to six carbon atoms, and loweralkenylloweralkyl; wherein each of R2 and R3 is independently selected from hydrido and loweralkyl; wherein each of R4 through R7, R10 and R11 is independently selected from hydrido, hydroxy, loweralkyl, benzyl, phenoxy, benzyloxy and haloloweralkyl; wherein n is a number selected from four through six; wherein p is a number selected from zero through four; wherein q is a number selected from three through five; wherein A is selected from phenyl, naphthyl and thienyl; wherein any of the foregoing A groups can be further substituted with one or more substituents independently selected from hydrido, hydroxy, loweralkyl, loweralkoxy, halo, haloloweralkyl, amino, monoloweralkylamino and diloweralkylamino; or a pharmaceutically acceptable salt thereof.
A PRACTICAL SYNTHESIS, OPTICAL RESOLUTION AND DETERMINATION OF ABSOLUTE CONFIGURATION OF ENANTIOMERICALLY PURE 1S,2R-(+)- AND 1R,2S-(-)-CIS-2-(1-PYRROLIDINYL)CYCLOHEXYLAMINES: IMPORTANT PRECURSORS FOR A NEW CLASS OF SIGMA-RECEPTOR LIGANDS AND ANTICONVULSANT DRUGS
Costa, Brian R. de,Radesca, Lilian
, p. 1837 - 1846 (2007/10/02)
Enantiomerically pure (+)- and (-)-cis-2-(1-pyrrolidinyl)cylohehexylamines ((+)- and (-)-4) were prepared starting with (+/-)-trans-2-aminocyclohexanol ((+/-)-5).The key step in the generation of the cis stereochemistry of (+)- and (-)-4 empolyed catalytic hydrogenation of the enamine mixture generated from condensation of pyrrolidine with (+/-)-2-(benzamido)cyclohexanone ((+/-)-7).An efficient optical resolution of (+/-)-4 was achieved through two recrystallizations of the mandelate salts.The absolute configuration of (+)- and (-)-4 was assigned as 1S,2R and 1R,2S,respectively, based on conversion of (-)-4 to and comparison with the N-methyl derivative (-)-13 of known 1R,2S absolute configuration.
