Base-controlled selectivity in the synthesis of linear and angular fused quinazolinones by a palladium-catalyzed carbonylation/nucleophilic aromatic substitution sequence.

A new approach for the facile synthesis of fused quinazolinone scaffolds through a palladium-catalyzed carbonylative coupling followed by an intramolecular nucleophilic aromatic substitution is described. The base serves as the key modulator: Whereas DBU gives rise to the linear isomers, Et3N promotes the preferential formation of angular products. Interestingly, a light-induced 4+4 reaction of the product was also observed.

[1]  Xiao‐Feng Wu,et al.  Recent advances in 4(3H)-quinazolinone syntheses , 2014 .

[2]  Bin Xu,et al.  Copper-Catalyzed Aerobic Oxidative Annulation and Carbon- Carbon Bond Cleavage of Arylacetamides: Domino Synthesis of Fused Quinazolinones , 2014 .

[3]  A. Chawla,et al.  RECENT ADVANCES OF QUINAZOLINONE DERIVATIVES AS MARKER FOR VARIOUS BIOLO GICAL ACTIVITIES , 2013 .

[4]  H. Neumann,et al.  Palladium-catalyzed oxidative carbonylation reactions. , 2013, ChemSusChem.

[5]  H. Neumann,et al.  Synthesis of heterocycles via palladium-catalyzed carbonylations. , 2013, Chemical reviews.

[6]  H. Neumann,et al.  Recent developments on the trifluoromethylation of (hetero)arenes. , 2012, Chemistry, an Asian journal.

[7]  F. Pfeffer,et al.  Asymmetric induction in domino Heck-aza-Michael reactions , 2012 .

[8]  Sahil Sharma,et al.  Vasicine and structurally related quinazolines , 2012, Medicinal Chemistry Research.

[9]  Hao Xu,et al.  Copper-catalyzed one-pot synthesis of imidazo/benzoimidazoquinazolinones by sequential Ullmann-type coupling and intramolecular C-H amidation. , 2012, Chemistry.

[10]  Thomas M. Chaloner,et al.  The Development of Domino Reactions Incorporating the Heck Reaction: The Formation of N‐Heterocycles , 2012 .

[11]  Aiwen Lei,et al.  Oxidative Carbonylierungen: Organometallverbindungen (RM) oder Kohlenwasserstoffe (RH) als Nucleophile , 2011 .

[12]  Qiang Liu,et al.  Oxidative carbonylation reactions: organometallic compounds (R-M) or hydrocarbons (R-H) as nucleophiles. , 2011, Angewandte Chemie.

[13]  H. Neumann,et al.  Palladium-catalyzed carbonylative coupling reactions between Ar-X and carbon nucleophiles. , 2011, Chemical Society reviews.

[14]  S. Martin,et al.  Multicomponent assembly strategies for the synthesis of diverse tetrahydroisoquinoline scaffolds. , 2011, Organic letters.

[15]  K. B. Sahu,et al.  A novel approach for the one-pot synthesis of linear and angular fused quinazolinones , 2011 .

[16]  V. Popik,et al.  Light-induced hetero-Diels-Alder cycloaddition: a facile and selective photoclick reaction. , 2011, Journal of the American Chemical Society.

[17]  F. Pfeffer,et al.  A general approach to N-heterocyclic scaffolds using domino Heck-aza-Michael reactions. , 2011, Organic & biomolecular chemistry.

[18]  B. Muller.  Multi-component Heterocycle Syntheses via Catalytic Generation of Alkynones , 2009 .

[19]  V. Charushin,et al.  Fluorine-containing heterocycles: XVIII. Monofluoro derivatives of quinazolines and 1,3-benzothiazin-4-ones , 2009 .

[20]  M. Beller,et al.  Palladiumkatalysierte Carbonylierungen von Arylhalogeniden und ähnlichen Substraten , 2009 .

[21]  H. Neumann,et al.  Palladium-catalyzed carbonylation reactions of aryl halides and related compounds. , 2009, Angewandte Chemie.

[22]  E. Merkul,et al.  Consecutive three-component synthesis of ynones by decarbonylative Sonogashira coupling. , 2009, Chemistry.

[23]  C. Barnard.  Palladium-Catalyzed Carbonylation—A Reaction Come of Age , 2008 .

[24]  V. Charushin,et al.  Synthesis and tuberculostatic activity of fluorine-containing derivatives of quinolone, quinazolinone, and benzothiazinone , 2008, Pharmaceutical Chemistry Journal.

[25]  T. Jeong,et al.  Progress in the Studies on Rutaecarpine , 2008, Molecules.

[26]  T. Müller,et al.  Multi-component syntheses of heterocycles by transition-metal catalysis. , 2007, Chemical Society reviews.

[27]  J. Mathias,et al.  Synthesis of substituted 2-amino-4-quinazolinones via ortho-fluorobenzoyl guanidines , 2006 .

[28]  M. Docampo,et al.  Microwave‐Promoted Ullmann Condensation of 2‐Aminopyridines with 2‐Chlorobenzoic Acids , 2006 .

[29]  H. Vélez-Castro,et al.  Synthesis of 9‐Methyl‐11H‐pyrido[2,1‐b]quinazolin‐11‐one Using the Ullmann Condensation , 2006 .

[30]  P. Guiry,et al.  Synthesis of Quinazolinones and Quinazolines , 2005 .

[31]  A. Rotaru,et al.  A Novel Coupling 1,3-Dipolar Cycloaddition Sequence as a Three-Component Approach to Highly Fluorescent Indolizines , 2005 .

[32]  V. Charushin,et al.  Stabilization of [2.2]paracyclophane anion as a result of transannular interaction , 2004 .

[33]  C. Bailly,et al.  Synthesis of condensed quinolines and quinazolines as DNA ligands. , 2004, Bioorganic & medicinal chemistry.

[34]  Sheng-Nan Wu,et al.  Rutaecarpine-induced block of delayed rectifier K+ current in NG108-15 neuronal cells , 2001, Neuropharmacology.

[35]  J. Mayer,et al.  A polymer-bound iminophosphorane approach for the synthesis of quinazolines. , 2001, Journal of combinatorial chemistry.

[36]  Bradley D. Smith,et al.  One-step synthesis of 4(3H)-quinazolinones , 2001 .

[37]  J. Sheu,et al.  Antithrombotic effect of rutaecarpine, an alkaloid isolated from Evodia rutaecarpa, on platelet plug formation in in vivo experiments , 2000, British journal of haematology.

[38]  A. Gopalsamy,et al.  Combinatorial synthesis of heterocycles: solid-phase synthesis of 2-amino-4(1H)-quinazolinone derivatives. , 2000, Journal of combinatorial chemistry.

[39]  L. Tietze,et al.  Multicomponent domino reactions for the synthesis of biologically active natural products and drugs , 2000, Medicinal research reviews.

[40]  J Ramis,et al.  New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones. , 1998, Journal of medicinal chemistry.

[41]  N. Liverton,et al.  Nonpeptide glycoprotein IIb/IIIa inhibitors: substituted quinazolinediones and quinazolinones as potent fibrinogen receptor antagonists. , 1998, Bioorganic & medicinal chemistry letters.

[42]  A. Bekhit,et al.  Non‐Steroidal Anti‐inflammatory Agents: Novel Pyrazolyl‐, 1,2‐Oxazolyl‐, and 1,3‐Diazinyl Derivatives of 4(3H)‐Quinazolinones , 1994, Archiv der Pharmazie.

[43]  W. Greenlee,et al.  A potent, orally active, balanced affinity angiotensin II AT1 antagonist and AT2 binding inhibitor. , 1993, Journal of medicinal chemistry.

[44]  A. Messmer,et al.  Synthesis, alkylation and ring opening of two differently fused pyridoquinazolones , 1990 .

[45]  D. J. Herzig,et al.  11-Oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid, an orally active antiallergy agent. , 1979, Journal of medicinal chemistry.