Indium Trichloride (InCl3) Catalyzed Synthesis of Fused 7-Azaindole Derivatives Using Domino Knoevenagel-Michael Reaction

An efficient and high yielding methodology developed for the synthesis of fused 7-azaindole derivatives via one pot multicomponent assembly process of cyclic 1,3-dicarbonyls with substituted aldehydes and 5-amino-1-tert-butyl-1H-pyrrole-3-carbonitrile. The transformation occurs via domino Knoevenagel- Michael reaction followed by intramolecular cyclization in the presence of catalytic amount of InCl3 (10 mol %). Mild reaction conditions, easy isolation of products, and good to excellent yields in a shorter period of time are the silent features of present methodology. Structures of all the newly prepared compounds have been corroborated by various spectroscopic methods.

[1]  Amol S. Kotmale,et al.  A catalyst- and solvent-free multicomponent synthesis of 7-azagramine analogues via a Mannich type reaction , 2016 .

[2]  B. Kim,et al.  One-pot synthesis of quinoxalines from reductive coupling of 2-nitroanilines and 1,2-diketones using indium , 2015 .

[3]  E. Suresh,et al.  Indium(III) chloride catalyzed highly diastereoselective domino synthesis of indenodithiepines and indenodithiocines. , 2015, Chemical communications.

[4]  P. Bonnet,et al.  The Azaindole Framework in the Design of Kinase Inhibitors , 2014, Molecules.

[5]  H. Chavan,et al.  Synthesis of 2,4,5-triaryl and 1,2,4,5-tetraaryl imidazoles using silica chloride as an efficient and recyclable catalyst under solvent-free conditions , 2014 .

[6]  B. Bandgar,et al.  An efficient and green method for the synthesis of [1,3]oxazine derivatives catalyzed by thiamine hydrochloride (VB1) in water , 2014 .

[7]  B. Bandgar,et al.  An Efficient Solvent-Free Synthesis of Naphthopyranopyrimidines Using Heteropolyacid as an Ecofriendly Catalyst , 2014 .

[8]  S. Routier,et al.  Recent advances in the synthesis and properties of 4-, 5-, 6- or 7-azaindoles , 2013 .

[9]  B. Bandgar,et al.  Aqueous Extract of Acacia concinna Pods: An Efficient Surfactant Type Catalyst for Synthesis of 3-Carboxycoumarins and Cinnamic Acids via Knoevenagel Condensation , 2013 .

[10]  Laurence Lafanechère,et al.  Azaindole derivatives are inhibitors of microtubule dynamics, with anti‐cancer and anti‐angiogenic activities , 2013, British journal of pharmacology.

[11]  Michael M. Cahill,et al.  Synthesis and identification of novel indolo[2,3-a]pyrimido[5,4-c]carbazoles as a new class of anti-cancer agents. , 2012, European journal of medicinal chemistry.

[12]  Hemant V Chavan,et al.  Synthesis, biological evaluation, and molecular docking of N-{3-[3-(9-methyl-9H-carbazol-3-yl)-acryloyl]-phenyl}-benzamide/amide derivatives as xanthine oxidase and tyrosinase inhibitors. , 2012, Bioorganic & medicinal chemistry.

[13]  S. Paul,et al.  An efficient green protocol for the synthesis of coumarin fused highly decorated indenodihydropyridyl and dihydropyridyl derivatives , 2012 .

[14]  B. Bandgar,et al.  Rapid One-pot, Four Component Synthesis of Pyranopyrazoles Using Heteropolyacid Under Solvent-free Condition , 2011 .

[15]  B. Bandgar,et al.  Polyethylene glycol in water: A simple, efficient and green protocol for the synthesis of quinoxalines , 2011 .

[16]  H. Hsieh,et al.  Scaffold-hopping strategy: synthesis and biological evaluation of 5,6-fused bicyclic heteroaromatics to identify orally bioavailable anticancer agents. , 2011, Journal of medicinal chemistry.

[17]  Eunji Lee,et al.  Supramolecular Architecture of 7-Azaindole Based Ag(I) Complexes , 2010 .

[18]  J. Menéndez,et al.  Multicomponent reactions for the synthesis of pyrroles. , 2010, Chemical Society reviews.

[19]  P. T. Perumal,et al.  InCl3 mediated one-pot multicomponent synthesis, anti-microbial, antioxidant and anticancer evaluation of 3-pyranyl indole derivatives. , 2010, Bioorganic & medicinal chemistry letters.

[20]  Suning Wang,et al.  Luminescence and reactivity of 7-azaindole derivatives and complexes. , 2010, Chemical Society reviews.

[21]  B. Bandgar,et al.  Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-alpha and IL-6 inhibitors with antioxidant activity. , 2010, Bioorganic & medicinal chemistry letters.

[22]  J. Yadav,et al.  Multi-Component Reactions Using Indium(III) Salts , 2010 .

[23]  Jihye Kim,et al.  Indium-mediated one-pot synthesis of benzoxazoles or oxazoles from 2-nitrophenols or 1-aryl-2-nitroethanones , 2009 .

[24]  C. Leblanc,et al.  7-Azaindole-3-acetic acid derivatives: potent and selective CRTh2 receptor antagonists. , 2009, Bioorganic & medicinal chemistry letters.

[25]  Xu-dong Cao,et al.  Synthesis of isoxazolo[5,4-b]pyridines by microwave-assisted multi-component reactions in water. , 2009, Journal of combinatorial chemistry.

[26]  Jared T Shaw,et al.  Cyclic anhydrides in formal cycloadditions and multicomponent reactions. , 2009, Chemical reviews.

[27]  B. Bandgar,et al.  Uncatalyzed Knoevenagel Condensation in PEG-600 at Room Temperature , 2008 .

[28]  T. Loh,et al.  Indium(III) iodide-mediated Strecker reaction in water: an efficient and environmentally friendly approach for the synthesis of α-aminonitrile via a three-component condensation , 2008 .

[29]  A. F. Hill,et al.  7-Azaindol-7-ylborate: A Novel Bidentate N^BH 3 Chelating Ligand , 2008 .

[30]  C. Kruse,et al.  7-Azaindole derivatives as potential partial nicotinic agonists. , 2008, Bioorganic & medicinal chemistry letters.

[31]  P. T. Perumal,et al.  An eco-friendly synthesis of 2-aminochromenes and indolyl chromenes catalyzed by InCl3 in aqueous media , 2007 .

[32]  Youngjin Kang,et al.  ( N -7-Azaindolyl)oligothiophenes: synthesis, characterization, and photophysical properties , 2007 .

[33]  Gil Hwan Ahn,et al.  Reductive heterocyclizations via indium-iodine-promoted conversion of 2-nitroaryl imines or 2-nitroarenes to 2,3-diaryl-substituted indazoles. , 2007, Organic & biomolecular chemistry.

[34]  Gil Hwan Ahn,et al.  Reductive heterocyclizations via indium/iodine-promoted one-pot conversion of 2-nitroaryl aldehydes, ketones, and imines , 2006 .

[35]  B. Kim,et al.  Indium-Mediated Reductive Cyclization of 2-Nitrochalcones to Quinolines , 2006 .

[36]  Jeffrey T. Kuethe,et al.  Practical methodologies for the synthesis of indoles. , 2006, Chemical reviews.

[37]  Jieping Zhu,et al.  Multicomponent Reactions: ZHU:MULTICOMPONENT REACTIONS O-BK , 2005 .

[38]  B. Hemmateenejad,et al.  Synthesis, cytotoxicity, QSAR, and intercalation study of new diindenopyridine derivatives. , 2004, Bioorganic & medicinal chemistry.

[39]  B. Kim,et al.  Indium-mediated Reductive Inter-molecular Coupling Reaction of 2-Nitroaniline with Aromatic Aldehydes to Benzimidazoles , 2004 .

[40]  Giuseppe Zampella,et al.  A practical synthesis of 7-azaindolylcarboxy-endo-tropanamide (DF 1012) , 2003 .

[41]  M. H. Babu,et al.  The indium(III) chloride-catalyzed von Pechmann reaction: a simple and effective procedure for the synthesis of 4-substituted coumarins , 2002 .

[42]  B. Ranu,et al.  Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: an improved procedure for the Biginelli reaction. , 2000, The Journal of organic chemistry.

[43]  T. Loh,et al.  Three Component Synthesis of β-Amino Carbonyl Compounds Using Indium Trichloride-Catalyzed One-pot Mannich-type Reaction in Water , 2000 .

[44]  Suning Wang,et al.  Syntheses, Structures, and Electroluminescence of New Blue/Green Luminescent Chelate Compounds: Zn(2-py-in)2(THF), BPh2(2-py-in), Be(2-py-in)2, and BPh2(2-py-aza) [2-py-in = 2-(2-pyridyl)indole; 2-py-aza = 2-(2-pyridyl)-7-azaindole] , 2000 .

[45]  B. Kim,et al.  Indium mediated reductive heterocyclization of 2-nitroacylbenzenes or 2-nitroiminobenzenes toward 2,1-benzisoxazoles in aqueous media , 2000 .

[46]  A. Baba,et al.  Indium trichloride catalyzed reductive Friedel-Crafts alkylation of aromatics using carbonyl compounds , 1998 .

[47]  E. LaVoie,et al.  Bioisosterism: A Rational Approach in Drug Design. , 1996, Chemical reviews.

[48]  T. Nishimura,et al.  The Catalytic Friedel-Crafts Acylation Reaction Using a Catalyst Generated from GaCl3 and a Silver Salt. , 1991 .

[49]  U. Schacht,et al.  2,3,4,4a,5,9b-Hexahydro-1H-indeno[1,2-b]pyridines: potential antidepressants. , 1984, Journal of medicinal chemistry.