- O-arylation versus C-arylation: Copper-catalyzed intramolecular coupling of aryl bromides with 1,3-dicarbonyls
-
The copper-catalyzed intramolecular coupling of aryl bromides with 1,3-dicarbonyls via a six-membered ring closure was examined. With CuI (10 mol %) as the catalyst, N,N′-dimethylethylenediamine as the ligand, and Cs2CO3 as the base,
- Fang, Yewen,Li, Chaozhong
-
-
Read Online
- Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones
-
The microbial reduction of β-ketoesters derived from 2-tetralone has been shown to produce good yields of 2-hydroxy-1-carboxy- or 3-hydroxy-2-carboxyesters. Baker's yeast invariably affords a high enantiomeric purity cis-hydroxyester, while fungi strains may produce, sometimes exclusively, cis- or trans- complementary stereochemistries. From a general survey of the baker's yeast reduction of cyclic β-ketoesters, a working model for predicting enantio- and diastereoselectivities of the reduction is proposed and discussed.
- Abalain, Cecile,Buisson, Didier,Azerad, Robert
-
-
Read Online
- 2,4-Diaminopyrimidines as dual ligands at the histamine H1 and H4 receptor - H1/H4-receptor selectivity
-
Distinct diaminopyrimidines, for example, 4-(4-methylpiperazin-1-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine are histamine H4 receptor (H4R) antagonists and show high affinity to the H4R, but only a moderate affinity to the
- Hammer, Sebastian G.,Gobleder, Susanne,Naporra, Franziska,Wittmann, Hans-Joachim,Elz, Sigurd,Heinrich, Markus R.,Strasser, Andrea
-
supporting information
p. 292 - 300
(2016/01/09)
-
- Mechanistic studies on the CAN-mediated intramolecular cyclization of δ-aryl-β-dicarbonyl compounds
-
The synthesis of 2-tetralones through the cyclization of δ-aryl-β-dicarbonyl substrates by using CAN is described. Appropriately functionalized aromatic substrates undergo intramolecular cyclizations generating 2-tetralone derivatives in moderate to good yields. DFT computational studies indicate that successful formation of 2-tetralones from δ-aryl-β-dicarbonyl radicals is dependent on the stability of the subsequent cyclohexadienyl radical intermediates. Furthermore, DFT computational studies were used to rationalize the observed site selectivity in the 2-tetralone products.
- Casey, Brian M.,Sadasivam, Dhandapani V.,Flowers II, Robert A.
-
p. 1472 - 1479
(2013/08/23)
-
- Palladium catalysed bis- and tris-cyclisations furnishing fused cyclopropyl carbo/heterocycles
-
Catalytic bis- and tris-cyclisation of a series of acyclic carbo- and heterocyclic precursors results in formation of two or three rings, two or three C-C bonds and two asymmetric tetrasubstituted C-centres regio- and stereoselectively in excellent yield.
- Grigg, Ronald,Sakee, Uthai,Sridharan, Visuvanathar,Sukirthalingam, Sukanthini,Thangavelauthum, Ravishanker
-
p. 9523 - 9532
(2007/10/03)
-
- 2-Amino-1-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors
-
Novel compounds are provided which are glycogen phosphorylase inhibitors which are useful in treating, preventing or slowing the progression of diseases requiring glycogen phosphorylase inhibitor therapy such as diabetes and related conditions (such as hy
- -
-
Page/Page column 17
(2008/06/13)
-
- cis- and trans-N-benzyl-octahydrobenzo[g]quinolines. Adrenergic and dopaminergic activity studies
-
In vitro assays on a series of cis- and trans-octahydrobenzo[g]quinolines indicated an unusual trend of affinities at the dopaminergic receptors and α adrenoceptors. The trans N-benzyl analogues exhibited affinity at the α2 as well as the D1-like receptors whereas their N-unsubstituted congeners showed a distinct preference for the α2 adrenoceptor. Enhanced activity for the α2 receptors was also exhibited by the cis N-benzylated isomers. These observations are interpreted by theoretical calculations.
- Thermos, Kyriaki,Froudakis, George E.,Tagmatarchis, Nikos,Katerinopoulos, Haralambos E
-
p. 883 - 886
(2007/10/03)
-
- Asymmetric palladium annulation: Formal synthesis of (+)-huperzine A
-
A new formal stereoselective synthesis of (+)-huperzine A 1 was achieved using as a key step a palladium mediated annulation between 2-methylene-1,3- propanediol diacetate and (1R,2S)-2-phenylcyclohexanol derived β-ketoester 14.
- Chassaing, Christophe,Haudrechy, Arnaud,Langlois, Yves
-
p. 8805 - 8809
(2007/10/03)
-
- A diastereoselective synthesis of trans/cis octahydronaphthoquinolizine
-
The tetracyclic system of 2,3,6,7,7a,8,12b,12c-octahydro-1H,5H-naphtho[1,2,3,i,j]quinolizine with trans/cis fusions of the B/D and B/C rings has been diastereospecifically synthesized in nine steps and in 23% total yield.
- Kouvarakis,Katerinopoulos
-
p. 3035 - 3044
(2007/10/03)
-
- Intramolecular oxygen versus carbon alkylation of naphthoate esters. A caveat on the mechanistic aspects of neocarzinostatin chemistry
-
α-Hydroxy naphthoate esters are shown to be capable of undergoing intramolecular alkylation at carbon as well as at both oxygen centers. Basic reaction conditions favor intramolecular oxygen alkylation of the phenol moiety in addition to intramolecular carbon alkylation leading to spirolactones. Chemistry in neutral or acidic media appears to proceed via γ-oxo ketene acetal intermediates that are converted to products derived from addition of water followed by cleavage of the resultant orthoacid. γ-Oxo ketene acetal intermediates derived from naphthoate esters are at least 40 times more reactive than those derived from simple β-keto esters. These studies give credence to the proposal that the α-hydroxy naphthoate moiety in neocarzinostatin is capable of participation during the epoxide-opening reaction. Mechanistic consequences of such participation are discussed.
- Lamothe, Marie,Fuchs
-
p. 4483 - 4496
(2007/10/02)
-
- Functionalised benzocyclo-octenones: Synthesis and chemistry
-
10,11-Dihydro-5-hydroxy-4-methoxycarbonylbenzo[5,6]cyclo-octa[1,2-c] furan-1,3-dione was selectively reduced and hydrolysed to 4,5-dihydrobenzo[5,6] cyclo-octa[1,2-c]furan-1,10(3H,11H)-dione whose structure was confirmed by X-ray analysis. Reduction and d
- Chenna, Ahmed,Donnelly, John,McCullough, Kevin J.,Proctor, George R.,Redpath, James
-
p. 261 - 270
(2007/10/02)
-
- SYNTHESE DU METHOXYCARBONYL-3 INDENE ET DE METHOXYCARBONYL-4 DIHYDRO-1,2 NAPHTALENES. OBTENTION DES β-TETRALONES A PARTIR DES α-TETRALONES CORRESPONDANTES
-
The synthesis of variously substituted 3-methoxycarbonylindene and 4-methoxycarbonyl-1,2-dihydronaphthalenes is described.A simple and efficient method for the transformation of 1-tetralone into 2-tetralone is reported.
- Vebrel, Joel,Carrie, Robert
-
p. 161 - 166
(2007/10/02)
-