A wide range of 2-aryl or 2-alkyl-substituted benzothiazoles are synthesized through intramolecular C(aryl)-S bond forming-cyclization using copper(II)-BINAM-catalyzed coupling of less reactive N-(2-chlorophenyl) benzo or alkylthioamide under mild reaction conditions (82 °C). © 2010 Elsevier Ltd. All rights reserved.

Govindasamy Sekar

Department Of Chemistry

D. J. C. Prasad

Arpan Dandapat

1,1' BINAPHTHYL 2,2' DIAMINE

2 PHENYLBENZOTHIAZOLE

benzothiazole derivative

CUPRIC ION

DIAMINE DERIVATIVE

N(2 CHLOROPHENYL)ARYLTHIOAMIDE

N(2 CHLOROPHENYL)BENZOTHIOAMIDE

THIOBENZAMIDE DERIVATIVE

unclassified drug

article

catalyst

chemical bond

chemical reaction

Cyclization

drug synthesis

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Tetrahedron Letters

A wide range of arylated alkynes are synthesized from the corresponding aryl halides and terminal alkynes through Sonogashira type cross-coupling reactions through C(aryl)-C bond formation in the presence of a catalytic amount of N,N′-dibenzyl BINAM-CuI complex under mild reaction conditions. © 2009 Elsevier Ltd. All rights reserved.

An efficient copper(I) complex catalyzed Sonogashira type cross-coupling of aryl halides with terminal alkynes

A wide range of N-arylated indoles are selectively synthesized through intermolecular C(aryl)-N bond formation from the corresponding aryl iodides and indoles through Ullmann-type coupling reactions in the presence of a catalytic amount of easily available N,N,N′,N′-tetramethyl-BINAM-CuI complex under very mild reaction conditions. © 2009 Elsevier Ltd. All rights reserved.

Tetrahedron

An efficient, mild, and selective Ullmann-type N-arylation of indoles catalyzed by copper(I) complex

Hexahydro-1H-phenothiazine moieties can be synthesized by domino aziridine ring opening with o-halothiophenols followed by copper-catalyzed Goldberg coupling-cyclization with good to excellent yields. Less reactive o-chlorothiophenols are also successfully utilized for the domino reaction to synthesize phenothiazine derivatives. This methodology is successfully applied in the synthesis of phenothiazine skeletons containing biologically active molecules such as antihistamine agents. © 2009 The Royal Society of Chemistry.

Organic and Biomolecular Chemistry

An efficient copper-catalyzed synthesis of hexahydro-1H- phenothiazines

Direct oxidation of primary alcohols to the corresponding carboxylic acids is performed highly efficiently at room temperature with anhydrous tert-butyl hydroperoxide in the presence of a catalytic amount of easily available CuCl under ligand free conditions in acetonitrile. Benzylic alcohols are more reactive than aliphatic alcohols, and these benzylic alcohols are selectively oxidized to the corresponding acids in the presence of aliphatic alcohols such as 1-octanol and 1-decanol. © 2008 Elsevier Ltd. All rights reserved.

CuCl catalyzed selective oxidation of primary alcohols to carboxylic acids with tert-butyl hydroperoxide at room temperature

A DABCO-copper(I) chloride complex (5 mol%) together with TEMPO (5 mol%) in nitromethane as solvent has been used as an efficient catalytic system for the selective oxidation of benzylic and allylic alcohols into the corresponding carbonyl compounds at room temperature where molecular oxygen acts as an ultimate, stoichiometric oxidant and water is the only by-product. The solidstate structure determination of the DABCOcopper complex shows that the copper is in the + II oxidation state with trigonal bipyramidal geometry and exists in a linear polymeric structure due to strong hydrogen bonding. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

Advanced Synthesis and Catalysis

Aerobic, chemoselective oxidation of alcohols to carbonyl compounds catalyzed by a DABCO-copper complex under mild conditions

An efficient copper(II)-catalyzed synthesis of benzothiazoles through intramolecular coupling-cyclization of N-(2-chlorophenyl)benzothioamides

Journal	Data powered by TypesetTetrahedron Letters
Publisher	Data powered by TypesetElsevier Ltd
ISSN	00404039
Open Access	No