Citation: LÜ Yue, MAO Shengxue, LI Fei, ZHU Xiaolei, LÜ Chengwei. Efficient Synthesis of 2-Amino-3-cyano-4H-pyran Derivatives via Catalyst-Free One-Pot Tri-Component Reaction[J]. Chinese Journal of Applied Chemistry, ;2018, 35(5): 518-525. doi: 10.11944/j.issn.1000-0518.2018.05.170220 shu

Efficient Synthesis of 2-Amino-3-cyano-4H-pyran Derivatives via Catalyst-Free One-Pot Tri-Component Reaction

LÜ Yue ^a ,
MAO Shengxue ^a ,
LI Fei ^a ,
ZHU Xiaolei ^b ,
LÜ Chengwei ^a,,

a.
College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China
b.
Teachers Training College of Anshan, Anshan, Liaoning 114000, China

Corresponding author: LÜ Chengwei, chengweilv@126.com
Received Date: 23 June 2017
Revised Date: 7 September 2017
Accepted Date: 18 October 2017

Fund Project: Supported by the National Natural Science Foundation of China(No.21403100), the Doctoral Scientific Research Foundation of Liaoning Province(No.20141100)the National Natural Science Foundation of China 21403100the Doctoral Scientific Research Foundation of Liaoning Province 20141100

Figures(1)

4H-Pyrans and 4H-pyran-annulated heterocyclic scaffolds are the key building blocks of numerous natural products and represent a "drug-like" structural motif with a broad spectrum of applications in organic synthesis and medicinal chemistry. In this paper, a convenient one-pot three-component strategy was conducted successfully under catalyst-free condition employing water as reaction medium and ethanol as co-solvent. Three kinds, over fifty 2-amino-3-cyano-4H-pyran derivatives were synthesized in good to excellent yields by the condensation of a series of aromatic aldehydes with malononitrile and different 1, 3-dicarbonyl compounds. Broad substrate scope, systematic characterization, eliminated catalyst, mild reaction condition, simple purification procedure are the best advantages in this methodology.
- multi-component reaction,
- catalyst-free,
- water,
- 4H-pyran derivatives,
- green synthesis
1. [1]
  Dekamin M G, Eslami M, Maleki A. Potassium Phthalimide-N-Oxyl:A Novel, Efficient, and Simple Organocatalyst for the One-pot Three-component Synthesis of Various 2-Amino-4H-Chromene Derivatives in Water[J]. Tetrahedron, 2013,69(3):1074-1085. doi: 10.1016/j.tet.2012.11.068
2. [2]
  Karami B, Kiani M. Silica-Supported Molybdic Acid:Preparation, Characterization, and Its Catalytic Application in Synthesis of Pyranocoumarins[J]. Monatsh Chem, 2016,147(6):1117-1124. doi: 10.1007/s00706-015-1551-3
3. [3]
  Zolfigol M A, Safaiee M, Bahrami-Nejad N. Dendrimeric Magnetic Nanoparticle Cores with Co-phthalocyanine Tags and Their Application in the Synthesis of Tetrahydrobenzo[b]pyran Derivatives[J]. New J Chem, 2016,40(6):5071-5079. doi: 10.1039/C6NJ00243A
4. [4]
  Bolognese A, Correale G, Manfra M. Antitumor Agents.3.Design, Synthesis, and Biological Evaluation of New Pyridoisoquinolindione and Dihydrothienoquinolindione Derivatives with Potent Cytotoxic Activity[J]. J Med Chem, 2004,47(4):849-858. doi: 10.1021/jm030918b
5. [5]
  Magar R L, Thorat P B, Jadhav V B. Silica Gel Supported Polyamine:A Versatile Catalyst for One Pot Synthesis of 2-Amino-4H-Chromene Derivatives[J]. J Mol Catal A Chem, 2013,374/375:118-124. doi: 10.1016/j.molcata.2013.03.022
6. [6]
  Tabassum S, Govindaraju S, Pasha M A. Ultrasound Mediated, Iodine Catalyzed Green Synthesis of Novel 2-Amino-3-Cyano-4H-Pyran Derivatives[J]. Ultrason Sonochem, 2015,24:1-7. doi: 10.1016/j.ultsonch.2014.12.006
7. [7]
  Bora P P, Bihani M, Bez G. Beyond Enzymatic Promiscuity:Asymmetric Induction by L-Proline on Lipase Catalyzed Synthesis of Polyfunctionalized 4H-Pyrans[J]. RSC Adv, 2015,5(62):50597-50603. doi: 10.1039/C5RA08785F
8. [8]
  Zolfigol M A, Yarie M, Baghery S. Application of {[4, 4'-BPyH] [C(CN)₃]₂} as a Bifunctional Nanostructured Molten Salt Catalyst for the Preparation of 2-Amino-4H-Chromene Derivatives under Solvent-free and Benign Conditions[J]. Synlett, 2016,27(9):1418-1422. doi: 10.1055/s-00000083
9. [9]
  Kiyani H, Jalali M S. Facile and Efficient Access to Tetrahydrobenzo[b]pyrans Catalyzed by N, N-Dimethylbenzylamine[J]. Heterocycles, 2016,92(1):75-85. doi: 10.3987/COM-15-13360
10. [10]
  Abbaspour-Gilandeh E, Aghaei-Hashjin M, Yahyazadeh A. (CTA)₃[SiW₁₂]-Li⁺-MMT:A Novel, Efficient and Simple Nanocatalyst for Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-4H-Chromene Derivatives via an Eco-Friendly Multicomponent Reaction in Water[J]. RSC Adv, 2016,6(60):55444-55462. doi: 10.1039/C6RA09818E
11. [11]
  Bayer T A, Schäfer S, Breyhan H. A Vicious Circle:Role of Oxidative Stress, Intraneuronal a Beta and Cu in Alzheimer's Disease[J]. Clin Neuropath, 2006,25(4):163-171.
12. [12]
  Beagley P, Blackie M A L, Chibale K. Synthesis and Antiplasmodial Activity in Vitro of New Ferrocene-Chloroquine Analogues[J]. Dalton Trans, 2003(15):3046-3051. doi: 10.1039/B303335J
13. [13]
  Kumar D, Reddy V B, Sharad S. A Facile One-Pot Green Synthesis and Antibacterial Activity of 2-Amino-4H-Pyrans and 2-Amino-5-Oxo-5, 6, 7, 8-Tetrahydro-4H-Chromenes[J]. Eur J Med Chem, 2009,44(9):3805-3809. doi: 10.1016/j.ejmech.2009.04.017
14. [14]
  Moghaddas M, Davoodnia A. Atom-Economy Click Synthesis of Tetrahydrobenzo[b]pyrans Using Cabon-Based Solid Acid as a Novel, Highly Efficient and Reusable Heterogeneous Catalyst[J]. Res Chem Intermed, 2015,41(7):4373-4386. doi: 10.1007/s11164-014-1536-6
15. [15]
  Heravi M M, Jani B A, Derikvand F. Three Component, One-Pot Synthesis of Dihydropyrano[3, 2-c]chromene Derivatives in the Presence of H₆P₂W₁₈O₆₂·18H₂O as a Green and Recyclable Catalyst[J]. Catal Commun, 2008,10(3):272-275. doi: 10.1016/j.catcom.2008.08.023
16. [16]
  Khurana J M, Kumar S. Tetrabutylammonium Bromide(TBAB):A Neutral and Efficient Catalyst for the Synthesis of Biscoumarin and 3, 4-Dihydropyrano[c]chromene Derivatives in Water and Solvent-free Conditions[J]. Tetrahedron Lett, 2009,50(28):4125-4127. doi: 10.1016/j.tetlet.2009.04.125
17. [17]
  Wang H J, Lu J, Zhang Z H. Highly Efficient Three-Component, One-Pot Synthesis of Dihydropyrano[3, 2-c]chromene Derivatives[J]. Monatsh Chem, 2010,141(10):1107-1112. doi: 10.1007/s00706-010-0383-4
18. [18]
  Khurana J M, Nand B, Saluja P. 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[J]. Tetrahedron, 2010,66(30):5637-5641. doi: 10.1016/j.tet.2010.05.082
19. [19]
  Banerjee S. The Remarkable Catalytic Activity of Ultra-Small Free-CeO₂ Nanoparticles in Selective Carbon-Carbon Bond Formation Reactions in Water at Room Temperature[J]. New J Chem, 2015,39(7):5350-5353. doi: 10.1039/C5NJ00500K
20. [20]
  Venkatesan K, Pujari S S, Srinivasan K V. Proline-Catalyzed Simple and Efficient Synthesis of 1, 8-Dioxo-decahydroacridines in Aqueous Ethanol Medium[J]. Synth Commun, 2009,39(2):228-241.
21. [21]
  Sadeh F N, Maghsoodlou M T, Hazeri N. A Facile and Efficient Synthesis of Tetrahydrobenzo[b]pyrans Using Lactose as a Green Catalyst[J]. Res Chem Intermed, 2015,41(8):5907-5914. doi: 10.1007/s11164-014-1710-x
22. [22]
  Seifi M, Sheibani H. 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[J]. Catal Lett, 2008,126(3):275-279.
23. [23]
  Albadi J, Mansournezhad A. Aqua-Mediated Multicomponent Synthesis of Various 4H-Pyran Derivatives Catalyzed by Poly-(4-Vinylpyridine)-Supported Copper Iodide Nanoparticle Catalyst[J]. Res Chem Intermed, 2016,42(6):5739-5752. doi: 10.1007/s11164-015-2400-z
24. [24]
  Amirheidari B, Seifi M, Abaszadeh M. Evaluation of Magnetically Recyclable Nano-Fe₃O₄ as a Green Catalyst for the Synthesis of Mono- and Bis-tetrahydro-4H-chromene and Mono and Bis 1, 4-Dihydropyridine Derivatives[J]. Res Chem Intermed, 2016,42(4):3413-3423. doi: 10.1007/s11164-015-2220-1
25. [25]
  Ahad A, Farooqui M. Organocatalyzed Domino Reactions:Diversity Oriented Synthesis of Pyran-Annulated Scaffolds Using in Situ-developed Benzylidenemalononitries[J]. Res Chem Intermed, 2017,43(4):2445-2455. doi: 10.1007/s11164-016-2772-8
26. [26]
  Kangani M, Hazeri N, Maghsoodlou M T. A Mild and Environmentally Benign Synthesis of Tetrahydrobenzo[b]pyrans and Pyrano[c]chromenes Using Pectin as a Green and Biodegrandable Catalyst[J]. J Chinese Chem Soc, 2016,63(11):896-901. doi: 10.1002/jccs.2016.63.issue-11
27. [27]
  Chen L, Bao S, Yang L. Cheap Thiamine Hydrochloride as Efficient Catalyst for Synthesis of 4H-Benzo[b]pyrans in Aqueous Ethanol[J]. Res Chem Intermed, 2017,43(7):3883-3891. doi: 10.1007/s11164-016-2843-x
28. [28]
  SHI Daqing, WANG Jing, ZHUANG Qiya. Three-Component One-Pot Synthesis of 1, 6-Dioxa-5-oxo-1, 4, 5, 6-tetrahydrophenanthrene Derivatives in Aqueous Media[J]. J Chinese Chem Soc, 2006,26(5):643-647.
29. [29]
  Niknam K, Piran A. Silica-Grafted Ionic Liquids as Recyclable Catalysts for the Synthesis of 3, 4-Dihydropyrano[c]chromenes and Pyrano[2, 3-c]pyrazoles[J]. Green Sustainable Chem, 2013,3(2):1-8. doi: 10.4236/gsc.2013.32A001
30. [30]
  Pore D M, Undale K A, Dongare B B. Potassium Phosphate Catalyzed a Rapid Three-component Synthesis of Tetrahydrobenzo[b]pyran at Ambient Temperature[J]. Catal Lett, 2009,132(1):104-108.
31. [31]
  Hasaninejad A, Shekouhy M, Golzar N. Silica Bonded N-Propyl-4-Aza-1-Azoniabicyclo[2.2.2]octane Chloride(SB-DABCO):A Highly Efficient, Reusable and New Heterogeneous Catalyst for the Synthesis of 4H-Benzo[b]pyran Derivatives[J]. Appl Catal A-Gen, 2011,402(1):11-22.
32. [32]
  Ren Y, Zhang W, Lu J. One-Pot Synthesis of Tetrahydro-4H-Chromenes by Supramolecular Catalysis in Water[J]. RSC Adv, 2015,5(97):79405-79412. doi: 10.1039/C5RA14385C
33. [33]
  Rajput J K, Arora P, Kaur G. CuFe₂O₄ Magnetic Heterogeneous Nanocatalyst:Low Power Sonochemical-Coprecipitation Preparation and Applications in Synthesis of 4H-Chromene-3-Carbonitrile Scaffolds[J]. Ultrason Sonochem, 2015,26:229-240. doi: 10.1016/j.ultsonch.2015.01.008
34. [34]
  Shirini F, Goli-Jolodar O, Akbari M. Preparation, Characterization, and Use of Poly(Vinylpyrrolidonium) Hydrogen Phosphate([PVP-H]H₂PO₄) as a New Heterogeneous Catalyst for Efficient Synthesis of 2-Amino-Tetrahydro-4H-Pyrans[J]. Res Chem Intermed, 2016,42(5):4733-4749. doi: 10.1007/s11164-015-2312-y
35. [35]
  Gu Y. Multicomponent Reactions in Unconventional Solvents:State of the Art[J]. Green Chem, 2012,14(8):2091-2128.
36. [36]
  Bodaghifard M A, Solimannejad M, Asadbegi S. Mild and Green Synthesis of Tetrahydrobenzopyran, Pyranopyrimidinone and Polyhydroquinoline Derivatives and DFT Study on Product Structures[J]. Res Chem Intermed, 2016,42(2):1165-1179. doi: 10.1007/s11164-015-2079-1
37. [37]
  Dömling A, Wang W, Wang K. Chemistry and Biology of Multicomponent Reactions[J]. Chem Rev, 2012,112(6):3083-3135. doi: 10.1021/cr100233r
38. [38]
  XIONG Xinquan, HAN Qian, SHI Lin. Application of Deep-Eutectic Solvents in Green Organic Synthesis[J]. Chinese J Org Chem, 2015,36(3):480-489.
39. [39]
  WEI Li, CHEN Xuwen, LIU Yunyun. Recent Advances in Organic Synthesis Employing Ethyl Lactate as Green Reaction Medium[J]. Chinese J Org Chem, 2016,36(5):954-961.
40. [40]
  Zhang Q, Vigier K D O, Royer S. Deep Eutectic Solvents:Syntheses, Properties and Applications[J]. Chem Soc Rev, 2012,41(21):7108-7146. doi: 10.1039/c2cs35178a
41. [41]
  Solhy A, Elmakssoudi A, Tahir R. Clean Chemical Synthesis of 2-Amino-Chromenes in Water Catalyzed by Nanostructured Diphosphate Na₂CaP₂O₇[J]. Green Chem, 2010,12(12):2261-2267. doi: 10.1039/c0gc00387e
42. [42]
  Dekamin M G, Eslami M. Highly Efficient Organocatalytic Synthesis of Diverse and Densely Functionalized 2-Amino-3-Cyano-4H-Pyrans under Mechanochemical Ball Milling[J]. Green Chem, 2014,16(12):4914-4921. doi: 10.1039/C4GC00411F
43. [43]
  Liu J, Lei M, Hu L. A Catalyst-free Reaction in Water:Synthesis of Benzo[4, 5]imidazo[1, 2-a]pyrimido[4, 5-d]pyrimidin-4(1H)-One Derivatives[J]. Green Chem, 2012,14(9):2534-2539. doi: 10.1039/c2gc35745c
44. [44]
  Yang H, Hu W, Deng S. Catalyst-Free Amidation of Aldehyde with Amine under Mild Conditions[J]. New J Chem, 2015,39(8):5912-5915. doi: 10.1039/C5NJ01372K
45. [45]
  Alonso D A, Baeza A, Chinchilla R. Deep Eutectic Solvents:The Organic Reaction Medium of the Century[J]. Eur J Org Chem, 2016,2016(4):612-632. doi: 10.1002/ejoc.201501197
46. [46]
  Gawande M B, Bonif Cio V D B, Luque R. Benign by Design:Catalyst-Free In-Water, On-Water Green Chemical Methodologies in Organic Synthesis[J]. Chem Soc Rev, 2013,42(12):5522-5551. doi: 10.1039/c3cs60025d
47. [47]
  Safaei H R, Shekouhy M, Rahmanpur S. Glycerol as a Biodegradable and Reusable Promoting Medium for the Catalyst-Free One-Pot Three Component Synthesis of 4H-Pyrans[J]. Green Chem, 2012,14(6):1696-1704. doi: 10.1039/c2gc35135h
48. [48]
  WANG Xicun, ZHANG Zhang, QUAN Zhengjun. Synthesis of N-Aryl-N'-(2-Benzofuroyl)thioureas and 1-Aroyl-4-(2'-Benzofuroyl)thiosemicarbazides in Aqueous Media[J]. Chinese J Org Chem, 2006,26(7):967-970.
49. [49]
  Xiao J, Wen H, Wang L. Catalyst-Free Dehydrative S_N1-type Reaction of Indolyl Alcohols with Diverse Nucleophiles "On Water"[J]. Green Chem, 2016,18(4):1032-1037. doi: 10.1039/C5GC01838B
50. [50]
  Bigi F, Carloni S, Ferrari L. Clean Synthesis in Water.Part 2:Uncatalysed Condensation Reaction of Meldrum's Acid and Aldehydes[J]. Tetrahedron Lett, 2001,42(31):5203-5205. doi: 10.1016/S0040-4039(01)00978-9
51. [51]
  Maggi R, Bigi F, Carloni S. Uncatalysed Reactions in Water:Part 2.Preparation of 3-Carboxycoumarins[J]. Green Chem, 2001,3(4):173-174. doi: 10.1039/b101822c
52. [52]
  Jin T S, Wang A Q, Wang X. A Clean One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives Catalyzed by Hexadecyltrimethyl Ammonium Bromide in Aqueous Media[J]. Synlett, 2004,2004(5):0871-0873.
53. [53]
  Patil D, Chandam D, Mulik A. Novel Brønsted Acidic Ionic Liquid ([CMIM] [CF₃COO]) Prompted Multicomponent Hantzsch Reaction for the Eco-Friendly Synthesis of Acridinediones:An Efficient and Recyclable Catalyst[J]. Catal Lett, 2014,144(5):949-958. doi: 10.1007/s10562-014-1202-z
54. [54]
  Brahmachari G, Banerjee B. 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[J]. ACS Sustainable Chem Eng, 2014,2(3):411-422. doi: 10.1021/sc400312n
55. [55]
  Chandam D R, Mulik A G, Patil P P. (±)-Camphor-10-Sulfonic Acid Catalyzed Atom Efficient and Green Synthesis of Triazolo[1, 2-a]indazole-Triones and Spiro Triazolo[1, 2-a]indazole-Tetraones[J]. Res Chem Intermed, 2015,41(2):761-771. doi: 10.1007/s11164-013-1226-9
56. [56]
  Shabalala N, Maddila S, Jonnalagadda S B. Catalyst-Free, One-Pot, Four-Component Green Synthesis of Functionalized 1-(2-Fluorophenyl)-1, 4-Dihydropyridines under Ultrasound Irradiation[J]. New J Chem, 2016,40(6):5107-5112. doi: 10.1039/C5NJ03574K
57. [57]
  Adib M, Yasaei Z, Mirzaei P. A One-pot, Multicomponent Synthesis of 5'-Amino-2, 2'-dioxospiro[indoline-3, 3'-pyrrole]-4'-carbonitriles[J]. Synlett, 2016,27(3):383-386.
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