A green, catalyst-free, solvent-free, high yielding one step synthesis of functionalized benzo[f]furo[3,2-c]chromen-4-(5H)-ones and furo[3,2-c]quinolin-4-(5H)-ones

A green, three-component reaction of 1-hydroxy-3H-benzo[f]chromen-3-ones and 4-hydroxyquinolin-2(1H)-ones, an aromatic aldehyde and isonitrile, was developed for the first time, which resulted in a variety of substituted functionalized benzo[f]furo[3,2-c]chromen-4-(5H)-ones and furo[3,2-c]quinolin-4-(5H)-ones in excellent yield. The merits of the presented protocol include the use of microwave irradiation, catalyst-free and solvent free conditions, high atom-efficiency and no need for work up or purification with column chromatography. The present method is milder yet more advanced than those previously reported for the synthesis of related structures, furo-chromen-4-ones, furopyrimidines, furopyranones etc. The synthesized compounds have been virtually screened against a series of therapeutic targets and have shown promising binding with some of them.

[1]  M. Don,et al.  Antitumor Agents. 239. Isolation, structure elucidation, total synthesis, and anti-breast cancer activity of neo-tanshinlactone from Salvia miltiorrhiza. , 2004, Journal of medicinal chemistry.

[2]  A. Shaabani,et al.  Microwave‐Assisted Three‐Component Condensation on Montmorillonite K10: Solvent‐Free Synthesis of Furopyrimidines, Furocoumarins, and Furopyranones , 2005 .

[3]  Hugues Bienaymé,et al.  A New Heterocyclic Multicomponent Reaction For the Combinatorial Synthesis of Fused 3-Aminoimidazoles. , 1998, Angewandte Chemie.

[4]  M. Hakkarainen,et al.  Microwave-Assisted Reaction in Green Solvents Recycles PHB to Functional Chemicals , 2014 .

[5]  M. Sigman,et al.  A General Catalyst for the Asymmetric Strecker Reaction This work was supported by the NIH (GM-43214). A postdoctoral fellowship to M.S.S. (NIH), and a predoctoral fellowship to P.V. sponsored by Alfred Bader are gratefully acknowledged. , 2000, Angewandte Chemie.

[6]  Kailai Xu,et al.  A computational study on the mechanism for the GaCl3-catalyzed [4+1] cycloaddition of α,β-unsaturated ketone and 2,6-dimethylphenyl isocyanide , 2005 .

[7]  B. Sondengam,et al.  Veprisinium salt, a novel antibacterial quaternary alkaloid from Vepris louisii. , 1982, Planta medica.

[8]  C. Viel,et al.  Alcaloïdes dihydrofuroquinoleiques de quelques rutaceae: Isolement, structure, proprietes biologiques , 1979 .

[9]  S. Ryu,et al.  Inhibition of mast cell degranulation by tanshinones from the roots of Salvia miltiorrhiza. , 1999, Planta medica.

[10]  Xiaofeng Liu,et al.  ChemMapper: a versatile web server for exploring pharmacology and chemical structure association based on molecular 3D similarity method , 2013, Bioinform..

[11]  T. Saegusa,et al.  A new approach for stereoselective synthesis of .gamma.-butyrolactones , 1982 .

[12]  Bruce Ganem,et al.  Strategies for innovation in multicomponent reaction design. , 2009, Accounts of chemical research.

[13]  L. A. Marcaurelle,et al.  Translational synthetic chemistry. , 2013, Nature chemical biology.

[14]  R. Menon,et al.  A facile three-component reaction involving [4+1] cycloaddition leading to furan annulated heterocycles ☆ , 2002 .

[15]  P. Anastas,et al.  Green Chemistry , 2018, Environmental Science.

[16]  Jie Wu.  General Microwave-assisted Protocols for the Expedient Synthesis of Furo[3,2-c]chromen-4-ones , 2006 .

[17]  L. Male,et al.  Microwave-mediated synthesis of an arylboronate library. , 2011, ACS combinatorial science.

[18]  Stewart A. Brown,et al.  The natural coumarins : occurrence, chemistry, and biochemistry , 1982 .

[19]  G. B. Williamson,et al.  Menthofurans from Calamintha ashei: effects on Schizachyrium scoparium and Lactuca sativa , 1988 .

[20]  A. Bardón,et al.  Two New Furanoeremophilanes from Senecio santelisis , 2010, Chemistry & biodiversity.

[21]  A. Shaabani,et al.  A Novel Three-Component Tetrahydrobenzofuran Synthesis , 2004 .

[22]  Xue‐Wei Liu,et al.  Microwave-enhanced one-pot synthesis of diversified 3-acyl-5-hydroxybenzofurans. , 2007, Journal of combinatorial chemistry.

[23]  Wen-liang Chang,et al.  Cytotoxic activities of tanshinones against human carcinoma cell lines. , 1991, The American journal of Chinese medicine.

[24]  E. V. Van der Eycken,et al.  The first palladium-catalyzed desulfitative Sonogashira-type cross-coupling of (hetero)aryl thioethers with terminal alkynes. , 2008, Organic letters.

[25]  A. Maleki,et al.  A novel class of extended pi-conjugated systems: one-pot synthesis of bis-3-aminoimidazo[1,2-a]pyridines, pyrimidines and pyrazines , 2009, Molecular Diversity.

[26]  M. Bayat,et al.  A Novel Approach for the Synthesis of Furopyrimidine and Oxobenzofuran Derivatives , 2010 .

[27]  D. G. Walker,et al.  Bis heteroannulation. 3. Facile synthesis of (.+-.)-ligularone and (.+-.)-petasalbine , 1981 .

[28]  Xuechen Li,et al.  A fascinating journey into history: exploration of the world of isonitriles en route to complex amides. , 2012, Angewandte Chemie.

[29]  I. Ugi,et al.  Multicomponent Reactions with Isocyanides. , 2000, Angewandte Chemie.

[30]  S. Murai,et al.  A GaCl3-Catalyzed [4+1] Cycloaddition of α,β-Unsaturated Carbonyl Compounds and Isocyanides Leading to Unsaturated γ-Lactone Derivatives , 2003 .

[31]  E. Cao,et al.  Effect of natural antioxidant tanshinone II-A on DNA damage by lipid peroxidation in liver cells. , 1996, Free radical biology & medicine.

[32]  A. Tolmachev,et al.  High throughput synthesis of extended pyrazolo[3,4-d]dihydropyrimidines. , 2012, ACS combinatorial science.

[33]  C. Kappe.  Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog. , 2000, Accounts of chemical research.

[34]  N. Chatani,et al.  Catalytic [4+1] Cycloaddition of α,β-Unsaturated Carbonyl Compounds with Isocyanides , 2005 .

[35]  A. Dömling.  Recent advances in isocyanide-based multicomponent chemistry. , 2002, Current opinion in chemical biology.

[36]  S. Ryu,et al.  In Vitro Cytotoxicity of Tanshinones from Salvia miltiorrhiza , 1997, Planta medica.

[37]  A. Blayo,et al.  Synthesis of 3,4,5-trisubstituted-1,2,4-triazoles. , 2010, Chemical reviews.

[38]  M Onitsuka,et al.  New platelet aggregation inhibitors from Tan-Shen; radix of Salvia miltiorrhiza Bunge. , 1983, Chemical & pharmaceutical bulletin.

[39]  N. Isambert,et al.  Multicomponent reactions and ionic liquids: a perfect synergy for eco-compatible heterocyclic synthesis. , 2011, Chemical Society reviews.

[40]  A. H. Meriçli,et al.  Eremophilane derivatives and other constituents from Mexican Senecio species , 1989 .

[41]  S. Pan,et al.  Catalytic three-component Ugi reaction. , 2008, Angewandte Chemie.