Convenient synthesis of benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles with 1 mol% CuCl2·2H2O as catalyst in water

A convenient and efficient procedure for the synthesis of benzo[4,5]thiazolo [2,3-c][1,2,4]triazoles has been developed via a tandem intermolecular C–N bond and intramolecular C–S bond formation sequence from o-bromo-arylisothiocyanates and aroylhydrazides. A series of benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles were provided in excellent overall yields with 1 mol% CuCl2·2H2O/1 mol% 1,10-phenanthroline as the catalyst and water as the solvent.

[1]  B. Ranu,et al.  Microwave-assisted simple and efficient ligand free copper nanoparticle catalyzed aryl-sulfur bond formation , 2007 .

[2]  Yunyun Liu,et al.  Tandem reactions initiated by copper-catalyzed cross-coupling: a new strategy towards heterocycle synthesis. , 2011, Organic & biomolecular chemistry.

[3]  Ri‐Yuan Tang,et al.  CuI/TMEDA-catalyzed annulation of 2-bromo alkynylbenzenes with Na2S: synthesis of benzo[b]thiophenes. , 2011, The Journal of organic chemistry.

[4]  Yuqiang Ding,et al.  Theoretical Study on Mechanism of Copper(I)-Catalyzed Cross-Coupling between Aryl Halides and Alkylamines , 2011 .

[5]  C. Xi,et al.  Concise approach to benzisothiazol-3(2H)-one via copper-catalyzed tandem reaction of o-bromobenzamide and potassium thiocyanate in water. , 2012, The Journal of organic chemistry.

[6]  V. Ananikov,et al.  The First Example of Polymer-Supported Palladium Catalyst for Stereo­selective S-S Bond Addition to Terminal Alkynes , 2005 .

[7]  Sunwoo Lee,et al.  One-pot synthesis of symmetrical and unsymmetrical aryl sulfides by Pd-catalyzed couplings of aryl halides and thioacetates. , 2011, The Journal of organic chemistry.

[8]  Yuyang Jiang,et al.  Efficient copper-catalyzed N-arylations of nitrogen-containing heterocycles and aliphatic amines in water , 2010 .

[9]  Marisa C. Kozlowski,et al.  Aerobic copper-catalyzed organic reactions. , 2013, Chemical reviews.

[10]  Ming Li,et al.  Three-component cascade annulation of β-ketothioamides promoted by CF3CH2OH: a regioselective synthesis of tetrasubstituted thiophenes. , 2013, Journal of Organic Chemistry.

[11]  E. V. Van der Eycken,et al.  C-N bond forming cross-coupling reactions: an overview. , 2013, Chemical Society reviews.

[12]  M. Simon,et al.  Green chemistry oriented organic synthesis in water. , 2012, Chemical Society reviews.

[13]  M. Yamaguchi,et al.  Equilibrating C-S bond formation by C-H and S-S bond metathesis. Rhodium-catalyzed alkylthiolation reaction of 1-alkynes with disulfides. , 2005, Journal of the American Chemical Society.

[14]  H. Liu,et al.  Efficient access to 1,4-benzothiazine: palladium-catalyzed double C-S bond formation using Na2S2O3 as sulfurating reagent. , 2013, Organic letters.

[15]  Fan Yang,et al.  Synthesis of unsymmetrical 2,2'-biindolyl derivatives by a Cu-catalyzed N-arylation/Pd-catalyzed direct arylation sequential process. , 2011, The Journal of organic chemistry.

[16]  G. Evano,et al.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. , 2008, Chemical reviews.

[17]  H. Fu,et al.  Copper-catalyzed synthesis of benzocarbazoles via α-C-arylation of ketones. , 2012, Chemical communications.

[18]  Olivier Jacquet,et al.  Cover Picture: A Diagonal Approach to Chemical Recycling of Carbon Dioxide: Organocatalytic Transformation for the Reductive Functionalization of CO2 (Angew. Chem. Int. Ed. 1/2012) , 2012 .

[19]  Junhua Li,et al.  A highly efficient Cu-catalyst system for N-arylation of azoles in water , 2012 .

[20]  L. Rout,et al.  Efficient CuO-nanoparticle-catalyzed C-S cross-coupling of thiols with iodobenzene. , 2007, Angewandte Chemie.

[21]  M. Wheeler Comparisons of fungal melanin biosynthesis in ascomycetous, imperfect and basidiomycetous fungi , 1983 .

[22]  Ming Li,et al.  Solvent-free and efficient synthesis of imidazo[1,2-a]pyridine derivatives via a one-pot three-component reaction , 2012 .

[23]  P. Ramamurthy,et al.  Photochemical Synthesis of s-Triazolo[3,4-b]benzothiazole and Mechanistic Studies on Benzothiazole Formation , 1997 .

[24]  Jie Wu,et al.  Synthesis of 2-(polyfluoroaryl)benzofurans via a copper(I)-catalyzed reaction of 2-(2,2-dibromovinyl)phenol with polyfluoroarene. , 2012, Organic letters.

[25]  Hui Yu,et al.  Copper-catalyzed synthesis of benzo[b]thiophenes and benzothiazoles using thiocarboxylic acids as a coupling partner. , 2013, The Journal of organic chemistry.

[26]  V. Ananikov,et al.  Nickel(II) Chloride-Catalyzed Regioselective Hydrothiolation of Alkynes , 2005 .

[27]  T. Ulven,et al.  Selective copper catalysed aromatic N-arylation in water , 2013 .

[28]  S. Nolan,et al.  Carbon-sulfur bond formation catalyzed by [Pd(IPr*(OMe))(cin)Cl] (cin = cinnamyl). , 2013, The Journal of organic chemistry.

[29]  D. Ma,et al.  Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles. , 2008, Accounts of chemical research.

[30]  Jie Wu,et al.  Route to pyrazolo[5,1-a]isoquinolines via a copper-catalyzed tandem reaction of 2-alkynylbromobenzene with pyrazole. , 2013, The Journal of organic chemistry.

[31]  C. Bolm,et al.  Mechanistic insights into copper-catalyzed Sonogashira-Hagihara-type cross-coupling reactions: sub-mol% catalyst loadings and ligand effects. , 2013, Chemistry.

[32]  Yuyang Jiang,et al.  Copper‐Catalyzed C‐Arylation and Denitrogenation of Tetrazoles: Domino Synthesis of 1,3‐Diaminoisoquinoline Derivatives , 2013 .

[33]  N. Jiao,et al.  Recent advances in copper-catalyzed dehydrogenative functionalization via a single electron transfer (SET) process. , 2012, Chemical Society reviews.

[34]  Di Wu,et al.  An efficient copper-catalyzed carbon-sulfur bond formation protocol in water. , 2011, Organic letters.

[35]  Xiu‐Liang Lv,et al.  One-pot multicomponent cascade reaction of N,S-ketene acetal: solvent-free synthesis of imidazo[1,2-a]thiochromeno[3,2-e]pyridines. , 2012, Organic letters.

[36]  M. Taillefer,et al.  Copper-catalyzed sonogashira-type reactions under mild palladium-free conditions. , 2008, Organic letters.

[37]  Zhenbang Lou,et al.  Concise Synthesis of 1-Naphthols under Mild Conditions through a Copper-Catalyzed Arylation of Methyl Ketones , 2014 .

[38]  M. Taillefer,et al.  A very simple copper-catalyzed synthesis of anilines by employing aqueous ammonia. , 2009, Angewandte Chemie.

[39]  Yun Liang,et al.  Copper-catalyzed double C-S bonds formation via different paths: synthesis of benzothiazoles from N-benzyl-2-iodoaniline and potassium sulfide. , 2014, Organic letters.

[40]  Yatao Qiu,et al.  Ligands for copper-catalyzed C-N bond forming reactions with 1 mol% CuBr as catalyst. , 2011, The Journal of organic chemistry.

[41]  V. Ananikov,et al.  Transition-metal-catalyzed C-S, C-Se, and C-Te bond formation via cross-coupling and atom-economic addition reactions. , 2011, Chemical reviews.

[42]  P. Saha,et al.  Copper-catalyzed domino intra- and intermolecular C-S cross-coupling reactions: synthesis of 2-(arylthio)arylcyanamides. , 2010, Organic letters.

[43]  Lian‐Hua Li,et al.  Copper-catalyzed synthesis of trifluoromethyl-substituted isoxazolines. , 2013, Chemical communications.

[44]  Yongwen Jiang,et al.  Synthesis of 3-substituted and 2,3-disubstituted quinazolinones via Cu-catalyzed aryl amidation. , 2012, Organic letters.

[45]  M. Taillefer,et al.  Direct copper-catalyzed α-arylation of benzyl phenyl ketones with aryl iodides: route towards tamoxifen. , 2012, Angewandte Chemie.

[46]  Ming Li,et al.  Switching regioselectivity of β-ketothioamides by means of iodine catalysis: synthesis of thiazolylidenes and 1,4-dithiines. , 2014, Chemistry.

[47]  Deping Wang,et al.  2-Pyridinyl beta-ketones as new ligands for room-temperature CuI-catalysed C-N coupling reactions. , 2009, Chemical communications.

[48]  H. Niu,et al.  Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water , 2014 .

[49]  V. Ananikov,et al.  Two distinct mechanisms of alkyne insertion into the metal-sulfur bond: combined experimental and theoretical study and application in catalysis. , 2010, Chemistry.

[50]  M. Yamaguchi,et al.  Rhodium-catalyzed methylthio transfer reaction between ketone alpha-positions: reversible single-bond metathesis of C-S and C-H bonds. , 2009, Organic letters.

[51]  J. Yadav,et al.  Iron(III) Chloride: A VersatileCatalyst for the Practical Synthesis of 3-Sulfenylindoles , 2009 .

[52]  Peng Xue,et al.  Efficient and economical access to substituted benzothiazoles: copper-catalyzed coupling of 2-haloanilides with metal sulfides and subsequent condensation. , 2009, Angewandte Chemie.

[53]  R. SanMartin,et al.  On-water chemistry: copper-catalyzed straightforward synthesis of benzo[b]furan derivatives in neat water. , 2006, Organic letters.

[54]  H. Nagasawa,et al.  Facile synthesis of 1,2,4-triazoles via a copper-catalyzed tandem addition-oxidative cyclization. , 2009, Journal of the American Chemical Society.

[55]  Xiu‐Liang Lv,et al.  ORGANIC LETTERS XXXX Vol . XX , No . XX 000 – 000 Direct Solvent-Free Regioselective Construction of Pyrrolo [ 1 , 2 ‐ a ] [ 1 , 10 ] phenanthrolines Based on Isocyanide-Based Multicomponent Reactions , 2013 .

[56]  M. Wheeler,et al.  Melanins and their importance in pathogenic fungi. , 1988, Current topics in medical mycology.

[57]  Copper(I)-catalyzed intramolecular O-arylation for the synthesis of 2,3,4,9-tetrahydro-1H-xanthen-1-ones with low loads of CuCl. , 2012, The Journal of organic chemistry.

[58]  M. Taillefer,et al.  Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions: copper makes a difference. , 2008, Angewandte Chemie.

[59]  C. Xi,et al.  Synthesis of 2-mercaptobenzothiazoles via DBU-promoted tandem reaction of o-haloanilines and carbon disulfide. , 2011, Organic letters.

[60]  C. Xi,et al.  Cu-catalyzed double S-alkenylation of potassium sulfide: a highly efficient method for the synthesis of various thiophenes. , 2010, Organic letters.