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

doi:10.11944/j.issn.1000-0518.2018.05.170220

Chinese Journal of Applied Chemistry ›› 2018, Vol. 35 ›› Issue (5): 518-525.DOI: 10.11944/j.issn.1000-0518.2018.05.170220

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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^*()

^aCollege of Chemistry and Chemical Engineering,Liaoning Normal University,Dalian,Liaoning 116029,China
^bTeachers Training College of Anshan,Anshan,Liaoning 114000,China

Received:2017-06-23 Accepted:2017-10-18 Published:2018-04-23 Online:2018-04-23
Contact: LÜ Chengwei
Supported by:
Supported by the National Natural Science Foundation of China(No.21403100), the Doctoral Scientific Research Foundation of Liaoning Province(No.20141100)

Abstract

Abstract:

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.

Key words: multi-component reaction, catalyst-free, water, 4H-pyran derivatives, green synthesis

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.

References

[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.
[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.
[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.
[4]	Bolognese A,Correale G,Manfra M,et al. 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.
[5]	Magar R L,Thorat P B,Jadhav V B,,et al. 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.
[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.
[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.
[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.
[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.
[10]	Abbaspour-Gilandeh E,Aghaei-Hashjin M,Yahyazadeh A,et al. (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.
[11]	Bayer T A,Schäfer S,Breyhan H,et al. 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]	Beagley P,Blackie M A L,Chibale K,et al. Synthesis and Antiplasmodial Activity in Vitro of New Ferrocene-Chloroquine Analogues[J]. Dalton Trans,2003,(15):3046-3051.
[13]	Kumar D,Reddy V B,Sharad S,et al. 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.
[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.
[15]	Heravi M M,Jani B A,Derikvand F,et al. 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.
[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.
[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.
[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.
[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.
[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]	Sadeh F N,Maghsoodlou M T,Hazeri N,et al. A Facile and Efficient Synthesis of Tetrahydrobenzo[b]pyrans Using Lactose as a Green Catalyst[J]. Res Chem Intermed,2015,41(8):5907-5914.
[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]	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.
[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.
[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.
[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.
[27]	Chen L,Bao S,Yang L,et al. 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.
[28]	SHI Daqing,WANG Jing,ZHUANG Qiya,et al. 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(in Chinese). 史达清,王静,庄启亚,等. 水介质中1,6-二氧-5-氧代-1,4,5,6-四氢化菲衍生物的三组分一锅合成[J]. 有机化学,2006,26(5):643-647.
[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.
[30]	Pore D M,Undale K A,Dongare B B,et al. Potassium Phosphate Catalyzed a Rapid Three-component Synthesis of Tetrahydrobenzo[b]pyran at Ambient Temperature[J]. Catal Lett,2009,132(1):104-108.
[31]	Hasaninejad A,Shekouhy M,Golzar N,et al. 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]	Ren Y,Zhang W,Lu J,et al. One-Pot Synthesis of Tetrahydro-4H-Chromenes by Supramolecular Catalysis in Water[J]. RSC Adv,2015,5(97):79405-79412.
[33]	Rajput J K,Arora P,Kaur G,et al. 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.
[34]	Shirini F,Goli-Jolodar O,Akbari M,et al. 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.
[35]	Gu Y.Multicomponent Reactions in Unconventional Solvents: State of the Art[J]. Green Chem,2012,14(8):2091-2128.
[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.
[37]	Dömling A,Wang W,Wang K.Chemistry and Biology of Multicomponent Reactions[J]. Chem Rev,2012,112(6):3083-3135.
[38]	XIONG Xinquan,HAN Qian,SHI Lin,et al. Application of Deep-Eutectic Solvents in Green Organic Synthesis[J]. Chinese J Org Chem,2015,36(3):480-489(in Chinese). 熊兴泉,韩骞,石霖,等. 低共熔溶剂在绿色有机合成中的应用[J]. 有机化学,2015,36(3):480-489.
[39]	WEI Li,CHEN Xuwen,LIU Yunyun,et al. Recent Advances in Organic Synthesis Employing Ethyl Lactate as Green Reaction Medium[J]. Chinese J Org Chem,2016,36(5):954-961(in Chinese). 韦丽,陈绪文,刘云云,等. 绿色反应介质乳酸乙酯在有机合成中的应用研究进展[J]. 有机化学,2016,36(5):954-961.
[40]	Zhang Q,Vigier K D O,Royer S,et al. Deep Eutectic Solvents:Syntheses, Properties and Applications[J]. Chem Soc Rev,2012,41(21):7108-7146.
[41]	Solhy A,Elmakssoudi A,Tahir R,et al. Clean Chemical Synthesis of 2-Amino-Chromenes in Water Catalyzed by Nanostructured Diphosphate Na2CaP2O7[J]. Green Chem,2010,12(12):2261-2267.
[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.
[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.
[44]	Yang H,Hu W,Deng S,et al. Catalyst-Free Amidation of Aldehyde with Amine under Mild Conditions[J]. New J Chem,2015,39(8):5912-5915.
[45]	Alonso D A,Baeza A,Chinchilla R,et al. Deep Eutectic Solvents:The Organic Reaction Medium of the Century[J]. Eur J Org Chem,2016,2016(4):612-632.
[46]	Gawande M B,Bonif Cio V D B,Luque R,et al. Benign by Design:Catalyst-Free In-Water, On-Water Green Chemical Methodologies in Organic Synthesis[J]. Chem Soc Rev,2013,42(12):5522-5551.
[47]	Safaei H R,Shekouhy M,Rahmanpur S,et al. 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.
[48]	WANG Xicun,ZHANG Zhang,QUAN Zhengjun,et al. 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(in Chinese). 王喜存,张彰,权正军,等. 水介质中N-芳基-N'-(2-苯并呋喃甲酰基)硫脲及1-芳甲酰基-4-(2'-苯并呋喃甲酰基)氨基硫脲的合成[J]. 有机化学,2006,26(7):967-970.
[49]	Xiao J,Wen H,Wang L,et al. Catalyst-Free Dehydrative SN1-type Reaction of Indolyl Alcohols with Diverse Nucleophiles “On Water”[J]. Green Chem,2016,18(4):1032-1037.
[50]	Bigi F,Carloni S,Ferrari L,et al. Clean Synthesis in Water.Part 2:Uncatalysed Condensation Reaction of Meldrum's Acid and Aldehydes[J]. Tetrahedron Lett,2001,42(31):5203-5205.
[51]	Maggi R,Bigi F,Carloni S,et al. Uncatalysed Reactions in Water:Part 2.Preparation of 3-Carboxycoumarins[J]. Green Chem,2001,3(4):173-174.
[52]	Jin T S,Wang A Q,Wang X,et al. 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]	Patil D,Chandam D,Mulik A,et al. 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.
[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.
[55]	Chandam D R,Mulik A G,Patil P P,et al. (±)-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.
[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.
[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.

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

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