4,4′-Trimethylenedipiperidine (TMDP): An Efficient Organocatalyst for the Mechanosynthesis of Pyrano[4,3-b]pyrans under Solid-state Conditions

References

• Jean-Louis Do and Tomislav Friščić, “Mechanochemistry: A Force of Synthesis,” ACS Central Science 3, no. 1 (2017): 13.
   PubMed Web of Science ®Google Scholar
• Marcos A. P. Martins, Clarissa P. Frizzo, Dayse N. Moreira, Lilian Buriol, and Pablo Machado, “Solvent-Free Heterocyclic Synthesis,” Chemical Reviews 109, no. 9 (2009): 4140.
   PubMed Web of Science ®Google Scholar
• B. Kubias, M. J. G. Fait, and R. Schlögl, “Mechanochemical Methods,” in Handbook of Heterogeneous Catalysis, edited by Ertl Gerhard, Knözinger Helmut, Schüth Ferdi, Weitkamp Jens, 2nd ed. (Weinheim: WileyVCH Verlag GmbH & Co. KGaA, 2008), 571–83.
   Google Scholar
• M. O. M'hamed, “Ball Milling for Heterocyclic Compounds Synthesis in Green Chemistry: A Review,” Synthetic Communications 45, no. 22 (2015): 2511.
   Web of Science ®Google Scholar
• Ana Lazuen Garay, Anne Pichon, and Stuart L. James, “Solvent-Free Synthesis of Metal Complexes,” Chemical Society Reviews 36, no. 6 (2007): 846.
   PubMed Web of Science ®Google Scholar
• Chi-Chieh Hsu, Nai-Chia Chen, Chien-Chen Lai, Yi-Hung Liu, Shie-Ming Peng, and Sheng-Hsien Chiu, “Solvent-Free Synthesis of the Smallest Rotaxane Prepared to Date,” Angewandte Chemie International Edition in English 47, no. 39 (2008): 7475.
   PubMed Web of Science ®Google Scholar
• Manuel Wilke, Maria Klimakow, Klaus Rademann, and Franziska Emmerling, “Fast and Efficient Synthesis of a Host Guest System: A Mechanochemical Approach,” CrystEngComm 18, no. 7 (2016): 1096.
   Web of Science ®Google Scholar
• Achim Stolle, Tony Szuppa, Silke E. S. Leonhardt, and Bernd Ondruschka, “Ball Milling in Organic Synthesis: Solutions and Challenges,” Chemical Society Reviews 40, no. 5 (2011): 2317.
   PubMed Web of Science ®Google Scholar
• Igor V. Magedov, Madhuri Manpadi, Marcia A. Ogasawara, Adriana S. Dhawan, Snezna Rogelj, Severine Van Slambrouck, Wim F. A. Steelant, Nikolai M. Evdokimov, Pavel Y. Uglinskii, Eerik M. Elias, et al. “Structural Simplification of Bioactive Natural Products with Multicomponent Synthesis. 2. Antiproliferative and Antitubulin Activities of Pyrano[3,2-c]Pyridones and Pyrano[3,2-c]Quinolones,” Journal of Medicinal Chemistry 51, no. 8 (2008): 2561.
   PubMed Web of Science ®Google Scholar
• Dinesh Kumar, Pooja Sharma, Harmanpreet Singh, Kunal Nepali, Girish Kumar Gupta, Subheet Kumar Jain, and Fidele Ntie-Kang, “The Value of Pyrans as Anticancer Scaffolds in Medicinal Chemistry." [In English],” RSC Advances 7, no. 59 (2017): 36977–99.
   Web of Science ®Google Scholar
• X. Fan, D. Feng, Y. Qu, X. Zhang, J. Wang, P. M. Loiseau, G. Andrei, R. Snoeck, and E. De Clercq, “Practical and Efficient Synthesis of Pyrano[3,2-C]Pyridone, Pyrano[4,3-B]Pyran and Their Hybrids with Nucleoside as Potential Antiviral and Antileishmanial Agents,” Bioorganic & Medicinal Chemistry Letters 20, no. 3 (2010): 809.
   PubMed Web of Science ®Google Scholar
• Mutlu Dilsiz Aytemir, Ünsal Çaliş, and Meral Özalp, “Synthesis and Evaluation of Anticonvulsant and Antimicrobial Activities of 3-Hydroxy-6-Methyl-2-Substituted 4h-Pyran-4-One Derivatives,” Archiv Der Pharmazie 337, no. 5 (2004): 281.
   PubMed Web of Science ®Google Scholar
• Renato L. T. Parreira, Odonı́rio Abrahão, and Sérgio E. Galembeck, “Conformational Preferences of Non-Nucleoside Hiv-1 Reverse Transcriptase Inhibitors,” Tetrahedron 57, no. 16 (2001): 3243.
   Web of Science ®Google Scholar
• L. Abrunhosa, M. Costa, F. Areias, A. Venancio, and F. Proenca, “Antifungal Activity of a Novel Chromene Dimer,” Journal of Industrial Microbiology & Biotechnology 34, no. 12 (2007): 787.
   PubMed Web of Science ®Google Scholar
• D. Rajguru, B. S. Keshwal, and S. Jain, “Solvent-Free, Green and Efficient Synthesis of Pyrano[4,3-b]Pyrans by Grinding and Their Biological Evaluation as Antitumor and Antioxidant Agents,” Medicinal Chemistry Research 22, no. 12 (2013): 5934.
   Web of Science ®Google Scholar
• X. S. Wang, J. X. Zhou, Z. S. Zeng, Y. L. Li, D. Q. Shi, and S. J. Tu, “One-Pot Synthesis of Pyrano[3,2-c]Pyran Derivatives Catalyzed by KF/Al2O3,” Arkivoc 11, (2006): 107.
   Web of Science ®Google Scholar
• D. Q. Shi, L. H. Niu, and Q. Y. Zhuang, “Synthesis of Pyrano[3,2-c]Pyran-5-One Derivatives by Three-Component One-Pot Reaction in Aqueous Media,” Chinese Journal of Organic Chemistry 28, no. 9 (2008): 1633.
   Web of Science ®Google Scholar
• Edmont Stoyanov, Ivo Ivanov, and Dieter Heber, “General Method for the Preparation of Substituted 2-Amino-4h,5h-Pyrano[4,3-B]Pyran-5-Ones and 2-Amino-4h-Pyrano[3,2-C]Pyridine-5-Ones,” Molecules 5, no. 12 (2000): 19.
   Web of Science ®Google Scholar
• Mohammad Seifi, and Hassan Sheibani, “High Surface Area Mgo as a Highly Effective Heterogeneous Base Catalyst for Three-Component Synthesis of Tetrahydrobenzopyran and 3,4-Dihydropyrano[c]Chromene Derivatives in Aqueous Media,” Catalysis Letters 126, no. 3–4 (2008): 275.
   Web of Science ®Google Scholar
• Jitender M. Khurana, Bhaskara Nand, and Pooja Saluja, “Dbu: A Highly Efficient Catalyst for One-Pot Synthesis of Substituted 3,4-Dihydropyrano[3,2-C]Chromenes, Dihydropyrano[4,3-B]Pyranes, 2-Amino-4h-Benzo[h]Chromenes and 2-Amino-4h Benzo[g]Chromenes in Aqueous Medium,” Tetrahedron 66, no. 30 (2010): 5637.
   Web of Science ®Google Scholar
• Deepika Rajguru, Balwant S. Keshwal, and Shubha Jain, “H6P2W18O62·18H2O: A Green and Reusable Catalyst for One-Pot Synthesis of Pyrano[4,3-b]Pyrans in Water,” Chinese Chemical Letters 24, no. 11 (2013): 1033.
   Web of Science ®Google Scholar
• Elaheh Mosaddegh, Asadollah Hassankhani, and Hassan Karimi-Maleh, “Synthesis and Characterization of ES/Cu(OH)2 Nanocomposite: A Novel and High Effective Catalyst in the Green Synthesis of Pyrano[4,3-b]Pyrans,” Materials Science and Engineering: C 46 (2015): 264.
   PubMed Web of Science ®Google Scholar
• Majid Ghashang, Syed Sheik Mansoor, and Krishnamoorthy Aswin, “Thiourea Dioxide: An Efficient and Reusable Organocatalyst for the Rapid One-Pot Synthesis of Pyrano[4,3-b]Pyran Derivatives in Water,” Chinese Journal of Catalysis 35, no. 1 (2014): 127.
   Web of Science ®Google Scholar
• N. G. Khaligh, “4-(Succinimido)-1-Butane Sulfonic Acid as a Bronsted Acid Catalyst for Synthesis of Pyrano[4,3-b]Pyran Derivatives under Solvent-Free Conditions,” Chinese Chemical Letters 26, no. 1 (2015): 26.
   PubMed Web of Science ®Google Scholar
• Elaheh Mosaddegh, and Asadollah Hassankhani, “Preparation and Characterization of Nano-Cao Based on Eggshell Waste: Novel and Green Catalytic Approach to Highly Efficient Synthesis of Pyrano[4,3-b]Pyrans,” Chinese Journal of Catalysis 35, no. 3 (2014): 351.
   Web of Science ®Google Scholar
• Nader Ghaffari Khaligh, “1'-Butylenebis(3-methyl-3H-Imidazol-1-ium) dihydrogensulfate as a Halogen-Free and Reusable Binuclear Bronsted Ionic Liquid Catalyzed the Synthesis of Pyrano[4,3-b]Pyran Derivatives,” Monatshefte Für Chemie - Chemical Monthly 145, no. 10 (2014): 1643. no.
   Google Scholar
• Michail N. Elinson, Ruslan F. Nasybullin, and Gennady I. Nikishin, “Electrocatalytic Efficient Multicomponent Approach to Medicinally Relevant Pyrano[4,3-b]Pyran Scaffold,” Electrocatalysis 4, no. 1 (2013): 56.
   Web of Science ®Google Scholar
• Deepika Rajguru, Balwant S. Keshwal, Shubha Jain, and Vasant W. Bhagwat, “Alum [KAl(SO4)(2)•12H2O]: a Green and Efficient Catalyst for Synthesis of Pyrano[4,3-b]Pyrans in Water under Conventional and Microwave Conditions,” Monatshefte Für Chemie - Chemical Monthly 144, no. 9 (2013): 1411.
   Google Scholar
• Xiao Chen, Weian Zhang, Fengjuan Yang, Chao Guo, Ziyuan Zhao, Di Ji, Fan Zhou, Zhi Wang, Rui Zhao, and Lei Wang, “Synthesis of Dihydropyrano[4,3-b]pyranes via a Multi Component Reaction Catalyzed by Lipase,” Green Chemistry Letters and Reviews 10, no. 1 (2017): 54.
   Web of Science ®Google Scholar
• Rao, R. N. M. V. N. K. Talluri, “An Overview of Recent Applications of Inductively Coupled Plasma-Mass Spectrometry (Icp-Ms) in Determination of Inorganic Impurities in Drugs and Pharmaceuticals,” Journal of Pharmaceutical and Biomedical Analysis 43, no. 1 (2007): 1–13.
   PubMed Web of Science ®Google Scholar
• Nader Ghaffari Khaligh, Hanna S. Abbo, and Salam J. J. Titinchi, “Synthesis of N-Methyl Imines in the Presence of Poly(N-Vinylpyridine) as a Reusable Solid Base Catalyst by a Mechanochemical Process,” Research on Chemical Intermediates 43, no. 2 (2017): 901.
   Web of Science ®Google Scholar
• Nader Ghaffari Khaligh, Sharifah Bee Abd Hamid, and Salam J. J. Titinchi, “Succinimide-N-Sulfonic Acid as a Recyclable Bronsted Acid Catalyst for Synthesis of Pyrano[4,3-b]Pyran Derivatives by Using Solar Energy under Solvent-Free Conditions,” Polycyclic Aromatic Compounds 37, no. 1 (2017): 31.
   Web of Science ®Google Scholar
• Nader Ghaffari Khaligh, Salam J. J. Titinchi, Sharifah Bee Abd Hamid, and Hanna S. Abbo, )“1-Butane Sulfonic Acid as a Bronsted Acid Catalyst for Synthesis of 4,4-(Arylmethylene)Bis(1H-Pyrazol-5-ol)S Derivatives under Solvent-Free Conditions,” Polycyclic Aromatic Compounds 36, no. 5 (2016): 716.
   Web of Science ®Google Scholar
• Nader Ghaffari Khaligh, Sharifah Bee Abd Hamid, and Salam J. J. Titinchi, “N-Methylimidazolium Perchlorate as a New Ionic Liquid for the Synthesis of Bis(pyrazol-5-ol)s under Solvent-Free Conditions,” Chinese Chemical Letters 27, no. 1 (2016): 104.
   Web of Science ®Google Scholar
• F. Schneider, A. Stolle, B. Ondruschka, and H. Hopf, “The Suzuki-Miyaura Reaction under Mechanochemical Conditions,” Organic Process Research & Development 13, no. 1 (2009): 44.
   Web of Science ®Google Scholar
• E. Abbaspour-Gilandeh, S. C. Azimi, K. Rad-Moghadam, and A. M. Barkchai, “[BMIm]BF4-LiCl: An Affective Catalytic System for the Synthesis of Pyrano[3,2-c]Chromene and Pyrano[4b]pyrone Derivatives,” Iranian Journal of Catalysis 3, no. 2 (2013): 3–91.
   Google Scholar
• Ellen V. Dalessandro, Hugo P. Collin, Luiz Gustavo L. Guimarães, Marcelo S. Valle, and Josefredo R. Pliego, Jr.“Mechanism of the Piperidine-Catalyzed Knoevenagel Condensation Reaction in Methanol: The Role of Iminium and Enolate Ions,” The Journal of Physical Chemistry B 121, no. 20 (2017): 5300.
   PubMed Web of Science ®Google Scholar
• G. Brahmachari, and B. Banerjee, “Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-3-cyano-4H-pyrans and Pyran-annulated Heterocyclic Scaffolds via an Eco-Friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst,” ACS Sustainable Chemistry & Engineering 2, no. 3 (2014): 411.
   Web of Science ®Google Scholar
• Ahmad Shaabani, Sima Samadi, Zahra Badri, and Abbas Rahmati, “Ionic Liquid Promoted Efficient and Rapid One-Pot Synthesis of Pyran Annulated Heterocyclic Systems,” Catalysis Letters 104, no. 1–2 (2005): 39.
   Web of Science ®Google Scholar
• A. Shaabani, S. Samadi, and A. Rahmati, “One-Pot, Three-Component Condensation Reaction in Water: An Efficient and Improved Procedure for the Synthesis of Pyran Annulated Heterocyclic Systems,” Synthetic Communications 37, no. 1–3 (2007): 491.
   Web of Science ®Google Scholar