Synthesis of Triindolylmethanes Catalyzed by Zeolites

Abstract Various triindolylmethanes were synthesized by condensation of indole (or its derivatives) with indole-3-carboxaldehyde using solid acids as catalysts. Among the valued catalysts, [SO3H]–MSU mesoporous molecular sieve-functionalized MSU with sulfonic acid group gave the most outstanding performance. Electron-donating groups on indoles were favourable to the reaction, whereas electron-withdrawing groups decreased the reactivity of indoles.

[1]  J. Čejka,et al.  ACID-CATALYZED SYNTHESIS OF MONO- AND DIALKYL BENZENES OVER ZEOLITES: ACTIVE SITES, ZEOLITE TOPOLOGY, AND REACTION MECHANISMS , 2002 .

[2]  J. Goodwin,et al.  Etherification on Zeolites: MTBE synthesis , 2002 .

[3]  M. Chakrabarty,et al.  Novel clay-mediated, tandem addition–elimination-(Michael) addition reactions of indoles with 3-formylindole: an eco-friendly route to symmetrical and unsymmetrical triindolylmethanes , 2002 .

[4]  D. MacMillan,et al.  Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis. , 2002, Journal of the American Chemical Society.

[5]  A. Cheetham,et al.  Direct observation of host-guest hydrogen bonding in the zeolite NaY/chloroform system by neutron scattering. , 2002, Journal of the American Chemical Society.

[6]  H. Teuber,et al.  Review on Reactions of Acetylacetaldehyde with Aromatic and Biogenic Amines and Indoles — Synthesis of Heterocycles via Hydroxymethylene Ketones , 2001 .

[7]  T. Kawase,et al.  Synthesis of novel cage molecules bicapped with tris(2-thienyl)methanes , 2001 .

[8]  M. Somei,et al.  Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. , 2001, Natural product reports.

[9]  C. Márquez-Álvarez,et al.  Combined Alkyl and Sulfonic Acid Functionalization of MCM-41-Type Silica: Part 1. Synthesis and Characterization , 2000 .

[10]  C. Márquez-Álvarez,et al.  Combined Alkyl and Sulfonic Acid Functionalization of MCM-41-Type Silica: Part 2. Esterification of Glycerol with Fatty Acids , 2000 .

[11]  G. Firestone,et al.  Ligand-independent activation of estrogen receptor function by 3, 3'-diindolylmethane in human breast cancer cells. , 2000, Biochemical pharmacology.

[12]  H. Yukawa,et al.  Indolyl Carboxylic Acids by Condensation of Indoles with α-Keto Acids , 2000 .

[13]  A. M. Almerico,et al.  From ascorbigens to indolocarbazoles , 1999 .

[14]  D. Williams,et al.  The anticarcinogen 3,3'-diindolylmethane is an inhibitor of cytochrome P-450. , 1995, Journal of biochemical toxicology.

[15]  J. Bergman.  Reactions of indoles with ortho esters, N,N-dimethylformamide and N,N-dimethylacetamide dialkyl acetals , 1985 .

[16]  U. Pindur,et al.  Reaktionen von elektronenreichen heterocyclen mit orthocarbonsäure‐derivaten. I. Zum reaktionsverhalten von acyclischen orthoestern mit indolen unter säurekatalyse , 1983 .

[17]  K. Arata,et al.  Reactions of butane and isobutane catalysed by titanium oxide treated with sulphate ion. Solid superacid catalyst , 1979 .

[18]  J. Bergman.  The reaction of some indoles with acetic-formic anhydride , 1971 .

[19]  C. Bahner,et al.  STYRYLQUINOLINE ANALOGS FROM HETEROCYCLIC CARBOXALDEHYDES. , 1965, Journal of medicinal chemistry.