DABCO-Promoted Cyclization of 2-Amino-4H-chromen-4-ones with 2,6-Dibenzylidenecyclohexan-1-ones for the Synthesis of Chromeno[2,3-b]tetrahydroquinoline.

DABCO-promoted cyclization reaction of substituted 2-amino-4H-chromen-4-ones with substituted 2,6-dibenzylidenecyclohexan-1-ones was investigated under mild conditions. This reaction provided a novel and efficient access to the 7,8,9,10-tetrahydro-12H-chromeno[2,3-b]quinolin-12-ones in good yields, the exocyclic double bond of which is predominantly E-selective.

[1]  T. Bíró,et al.  Knoevenagel‐Cyclization Cascade Reactions of Substituted 5,6‐Dihydro‐2 H ‐Pyran Derivatives , 2021, European Journal of Organic Chemistry.

[2]  Huimyoung Byeon,et al.  Substrate‐Controlled Chemo‐/Enantioselective Synthesis of α‐Benzylated Enals and Chiral Cyclopropane‐Fused 2‐Chromanone Derivatives , 2021, Advanced Synthesis & Catalysis.

[3]  Huicai Huang,et al.  Organocatalytic β,γ-Selective Activation of Deconjugated Butenolides Access to Chiral Tricyclic Chroman-butyrolactones. , 2021, The Journal of organic chemistry.

[4]  Ying Han,et al.  Water Modulated Diastereoselective Synthesis of cis/trans-Spiro[indoline-3,6'-naphtho[2,3-c]carbazoles]. , 2021, The Journal of organic chemistry.

[5]  Cunde Wang,et al.  Piperidine-Mediated [3 + 3] Cyclization of 2-Amino-4H-chromen-4-ones and 2-Benzylidenemalononitriles: To Access 2-Aminochromeno[2,3-b]pyridine Derivatives. , 2021, The Journal of organic chemistry.

[6]  Jingxuan Chen,et al.  Efficient Synthesis and Bioevaluation of Novel Dual Tubulin/Histone Deacetylase 3 Inhibitors as Potential Anticancer Agents. , 2021, Journal of medicinal chemistry.

[7]  Nitin Kumar,et al.  Progress and development of C-3, C-6, and N-9 position substituted carbazole integrated molecular hybrid molecules as potential anticancer agents. , 2021, Mini reviews in medicinal chemistry.

[8]  M. Szostak,et al.  Recent Advances in Metal‐Catalyzed Functionalization of Indoles , 2021 .

[9]  Yang Wang,et al.  Diastereoselective Synthesis of Tetrahydrospiro[carbazole-1,3'-indolines] via an InBr3-Catalyzed Domino Diels-Alder Reaction. , 2021, The Journal of organic chemistry.

[10]  Anil Kumar Garige,et al.  Molecular hybridization based design and synthesis of new benzo[5,6]chromeno[2,3-b]-quinolin-13(14H)-one analogs as cholinesterase inhibitors , 2021, Medicinal Chemistry Research.

[11]  Cunde Wang,et al.  DBU-Promoted Cascade Selective Nucleophilic Addition/C-C Bond Cleavage/Hetero-Diels-Alder Reactions of 2-Amino-4H-chromen-4-ones with β-Nitrostyrenes and/or Aryl Aldehydes: Access to 5H-Chromeno[2,3-b]pyridin-5-ones. , 2020, The Journal of organic chemistry.

[12]  M. Ibrahim,et al.  Synthesis and antimicrobial evaluation of the novel heteroannulated furo[3′,2′:6,7]chromeno[2,3‐b]pyridines: Part 1 , 2020 .

[13]  S. Lorkowski,et al.  Diversity of Chromanol and Chromenol Structures and Functions: An Emerging Class of Anti-Inflammatory and Anti-Carcinogenic Agents , 2020, Frontiers in Pharmacology.

[14]  L. Kaviarasan,et al.  Molecular docking studies and synthesis of a new class of chroman-4-one fused 1,3,4-thiadiazole derivatives and evaluation for their anticancer potential , 2020, Journal of the Iranian Chemical Society.

[15]  Yangmin Ma,et al.  Synthesis of C6-Substituted Isoquinolino[1,2-b]quinazolines via Rh(III)-Catalyzed C-H Annulation with Sulfoxonium Ylides. , 2020, The Journal of organic chemistry.

[16]  Chaoguo Yan,et al.  Construction of Spiro[indoline-3,3′-pyridazines] and Spiro[indene-2,3′-pyridazines] via TEMPO-Mediated Oxidative Aza-Diels-Alder Reactions , 2019, European Journal of Organic Chemistry.

[17]  M. Sarg,et al.  Facile Synthesis and Anticancer Activity Study of Novel Series of Substituted and Fused Coumarin Derivatives , 2018 .

[18]  Jing Sun,et al.  Selective Synthesis of 3-(9 H-Carbazol-2-yl)indolin-2-ones and Spiro[tetrahydrocarbazole-3,3'-oxindoles] via a HOTf Catalyzed Three-Component Reaction. , 2018, The Journal of organic chemistry.

[19]  N. M. El-Gohary,et al.  Synthesis, molecular, electronic structure, linear and non-linear optical and phototransient properties of 8-methyl-1,2-dihydro-4H-chromeno[2,3-b]quinoline-4,6(3H)-dione (MDCQD): Experimental and DFT investigations. , 2018, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[20]  C. Godugu,et al.  A Review on Pharmacological Properties of Coumarins. , 2018, Mini reviews in medicinal chemistry.

[21]  D. Jun,et al.  Synthesis, Biological Assessment and Molecular Modeling of Racemic QuinoPyranoTacrines for Alzheimer's Disease Therapy , 2018 .

[22]  J. Marco-Contelles,et al.  New Tacrines as Anti-Alzheimer's Disease Agents. The (Benzo)Chromeno- PyranoTacrines. , 2018, Current topics in medicinal chemistry.

[23]  Jing Sun,et al.  TfOH-Catalyzed One-Pot Domino Reaction for Diastereoselective Synthesis of Polysubstituted Tetrahydrospiro[carbazole-1,3'-indoline]s. , 2017, The Journal of organic chemistry.

[24]  S. Mobin,et al.  Efficient Cu(OTf)2-catalyzed and microwave-assisted rapid synthesis of 3,4-fused chromenopyridinones under neat conditions , 2017 .

[25]  Yuan Sun,et al.  Designing multi-targeted agents: An emerging anticancer drug discovery paradigm. , 2017, European journal of medicinal chemistry.

[26]  S. Damavandi.  A novel four-component route to synthesis 11-amino-12-(4-aryl)-8,9,10,12-tetrahydro-7H-chromeno[2,3-b]quinolin-3-ol derivatives , 2016 .

[27]  A. Ghoneim,et al.  Synthesis and biological activities of some fused pyran derivatives , 2016 .

[28]  N. M. El-Gohary,et al.  Chemical Transformations of Chromone-3-carbonitrile with Cyclohexanediones: Synthesis of Bis[1]chromenophenanthrolines , 2016 .

[29]  L. Mammino.  A Computational Study of Euglobal G1 - An Acylphloroglucinol with Anticancer Activity , 2014 .

[30]  A. Kamal,et al.  The design and development of imidazothiazole–chalcone derivatives as potential anticancer drugs , 2013, Expert opinion on drug discovery.

[31]  C. Pérez,et al.  Synthesis, biological assessment, and molecular modeling of racemic 7-aryl-9,10,11,12-tetrahydro-7H-benzo[7,8]chromeno[2,3-b]quinolin-8-amines as potential drugs for the treatment of Alzheimer's disease. , 2012, European journal of medicinal chemistry.

[32]  A. Venkatesham,et al.  Synthesis of new chromeno-annulated cis-fused pyrano[3,4-c]pyran derivatives via domino Knoevenagel–hetero-Diels–Alder reactions and their biological evaluation towards antiproliferative activity , 2012 .

[33]  Artem Cherkasov,et al.  Targeting the binding function 3 (BF3) site of the human androgen receptor through virtual screening. , 2011, Journal of medicinal chemistry.

[34]  A. Morreale,et al.  Synthesis, biological assessment and molecular modeling of 14-aryl-10,11,12,14-tetrahydro-9H-benzo[5,6]chromeno[2,3-b]quinolin-13-amines. , 2011, Bioorganic & medicinal chemistry letters.

[35]  S. S. Bisht,et al.  Search of antimycobacterial activities in hybrid molecules with benzopyran skeleton , 2011, Medicinal Chemistry Research.

[36]  B. Dash,et al.  Codrug: an efficient approach for drug optimization. , 2010, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[37]  E. Sieber-McMaster,et al.  Design and synthesis of potent inhibitors of cholesteryl ester transfer protein (CETP) exploiting a 1,2,3,4-tetrahydroquinoline platform. , 2009, Bioorganic & medicinal chemistry letters.

[38]  F. Badria,et al.  Design and synthesis of azolopyrimidoquinolines, pyrimidoquinazolines as anti-oxidant, anti-inflammatory and analgesic activities. , 2009, European journal of medicinal chemistry.

[39]  V. Karapetyan,et al.  Synthesis of 1-azaxanthones by condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-(cyano)benzopyrylium triflates and subsequent domino ‘retro-Michael/nitrile-addition/heterocyclization’ reaction , 2008 .

[40]  Chung‐Ming Sun,et al.  Synthesis and biological evaluation of novel angularly fused polycyclic coumarins. , 2005, Bioorganic & medicinal chemistry letters.

[41]  S. Saha,et al.  Synthesis of 2,2'-diaminobischromones using a modified procedure for the rearrangement of 5-(2-hydroxyphenyl)isoxazole to 2-aminochromone , 2005 .

[42]  E Uriarte,et al.  Simple coumarins and analogues in medicinal chemistry: occurrence, synthesis and biological activity. , 2005, Current medicinal chemistry.

[43]  R. Crossley,et al.  Synthesis and antiinflammatory activity of certain 5,6,7,8-tetrahydroquinolines and related compounds. , 1995, Journal of medicinal chemistry.

[44]  Joel Morris,et al.  A novel synthesis of 2-aminochromones via phosgeniminium salts , 1992 .