Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

• Vladimir N. Boiko

Beilstein J. Org. Chem. 2010, 6, 880–921, doi:10.3762/bjoc.6.88

• heterocyclic compounds using trifluoromethylthiocopper (Scheme 23). The reaction is carried out by heating in a polar solvent (e.g. DMF, quinoline or N-methyl pyrrolidone) and the substrate can contain electron-donating or electron-withdrawing groups. Electron-withdrawing groups activate the iodo atom and

Synthesis of gem-difluoromethylenated analogues of boronolide

• Jing Lin,
• Xiao-Long Qiu and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2010, 6, No. 37, doi:10.3762/bjoc.6.37

• attempts to convert the triple bond in compound 12a into the cis double bond via hydrogenation in the presence of Lindlar catalyst were unsuccessful. Even with the addition of quinoline, these reactions only resulted in inseparable mixtures. Fortunately, hydrogenation proceeded well by means of Pd–BaSO4

• –quinoline system [26], leading to the expected alcohol 13a in 96% yield. Subsequent selective removal of the primary TBS group in 13a with D-camphor-10-sulfonic acid (CSA) yielded the diol 14a in 80% yield. As expected, treatment of compound 14a with 0.2 equiv of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO

Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones

• Heloise Brice,
• Jonathan Clayden and
• Stuart D. Hamilton

Beilstein J. Org. Chem. 2010, 6, No. 22, doi:10.3762/bjoc.6.22

• : bicyclic; cyclisation; dearomatisation; enol ether; heterocycle; pyridine; quinoline; Introduction Oxidative [1][2][3] or reductive (nucleophilic) [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] dearomatising cyclisation reactions are effective strategies for rapidly building complexity

An enantiomerically pure siderophore type ligand for the diastereoselective 1 : 1 complexation of lanthanide(III) ions

• Markus Albrecht,
• Olga Osetska,
• Thomas Abel,
• Gebhard Haberhauer and
• Eva Ziegler

Beilstein J. Org. Chem. 2009, 5, No. 78, doi:10.3762/bjoc.5.78

• peptidic scaffold and the final ligand 1a-H3 is obtained in good yield (90%). Successive Cope rearrangement of the spacers to the 5-position of the quinoline moiety is not observed under the chosen reaction conditions. 1H NMR spectra of 4 and 1a-H3 show pronounced differences for the resonances of the 8

Regioselective alkynylation followed by Suzuki coupling of 2,4-dichloroquinoline: Synthesis of 2-alkynyl- 4-arylquinolines

• Ellanki A. Reddy,
• Aminul Islam,
• K. Mukkanti,
• Venkanna Bandameedi,
• Dipal R. Bhowmik and
• Manojit Pal

Beilstein J. Org. Chem. 2009, 5, No. 32, doi:10.3762/bjoc.5.32

• -dichloroquinoline; palladium; water; Introduction 2-Alkynyl pyridine and its benzo (i.e. quinoline) derivative possessing an aryl group at the C-4 position (A, Figure 1) have attracted considerable interest due to their utility in the development of compounds of potential pharmacological interest [1][2][3]. 2

• -Alkenyl/alkynylquinolines, have been reported to possess anti-retroviral properties [4]. Only few methods are known for the synthesis of A. Considering the possible C–C bond forming reactions on a pyridine/quinoline ring (Figure 1), the synthesis of A can be carried out following two main strategies e.g

• . (a) arylation at C-4 followed by alkynylation at C-2 or (b) alkynylation at C-2 followed by arylation at C-4. Methodologies based on strategy ‘a’ have been reported earlier. For example, Sonogashira coupling of a terminal alkyne with 2-chloro-4-aryl substituted quinoline [3] in the presence of (PPh3

Quinoline based receptor in fluorometric discrimination of carboxylic acids

• Kumaresh Ghosh,
• Suman Adhikari,
• Asoke P. Chattopadhyay and
• Purnendu Roy Chowdhury

Beilstein J. Org. Chem. 2008, 4, No. 52, doi:10.3762/bjoc.4.52

• Kumaresh Ghosh Suman Adhikari Asoke P. Chattopadhyay Purnendu Roy Chowdhury Department of Chemistry, University of Kalyani, Kalyani, Nadia-741235, India Chembiotek Research International Pvt. Ltd., Salt Lake City, Kolkata-700 091, India 10.3762/bjoc.4.52 Abstract Quinoline and naphthalene-based

• value and did not form any excimer upon complexation with the same acids under similar conditions. This established the role of quinoline ring nitrogen in binding with the acids. Keywords: carboxylic acid recognition; excimer emission; naphthalene; quinoline; Introduction The sensing and monitoring of

• - and dicarboxylic acids by a large number of receptors of different architectures is known [11][12][13][14]. We have also reported a series of synthetic receptors for carboxylic acids of various types [15][16][17][18]. In continuation, we report here a new quinoline based sensor 1 (Figure 1) which is

New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline- 2,4(1H,3H)-dione compounds

• Oldřich Paleta,
• Karel Pomeisl,
• Stanislav Kafka,
• Antonín Klásek and
• Vladislav Kubelka

Beilstein J. Org. Chem. 2005, 1, No. 17, doi:10.1186/1860-5397-1-17

• 72 Zlín, Czech Republic Zentiva, U Kabelovny 130, 10237 Prague 10, Czech Republic 10.1186/1860-5397-1-17 Abstract Substituted 3-(fluoroacyloxy)quinoline-2,4(1H,3H)-diones including 3-(fluoroiodoacetoxy) derivatives react with triethyl phosphite to afford either the product of the Perkow reaction or

• the corresponding 4-ethoxyquinolin-2(1H)-one. In both reactions, the fluorocarboxylate anion acts as the first observed leaving group. This observation restricts the application of the intramolecular Horner-Wadsworth-Emmons synthesis to modify quinoline-2,4(1H,3H)-diones by the annulation of

• the sugar skeleton and its multiple acetoxy groups. In this communication we would like to report on the ability of halocarboxylate anions to act as leaving groups in the reactions of 3-(haloacyloxy)-quinoline-2,4(1H,3H)-diones with triethyl phosphite to afford 8 and 9, the products of the Perkow