Citation: Vijaykumar M. Joshi, Rupali L. Magar, Prashant B. Throat, Sunil U. Tekale, Bhagavan R. Patil, Mangal P. Kale, Rajendra P. Pawar. Novel one-pot synthesis of 4H-chromene derivatives using amino functionalized silica gel catalyst[J]. Chinese Chemical Letters, ;2014, 25(3): 455-458. doi: 10.1016/j.cclet.2013.12.016 shu

Novel one-pot synthesis of 4H-chromene derivatives using amino functionalized silica gel catalyst

1.
a Department of Chemistry, Karmveer Ramraoji Aher Arts, Science and Commerce College, Deola 423 105, MS, India;
2.
b Department of Chemistry, Deogiri College, Aurangabad 431 005, MS, India;
3.
c Department of Chemistry, Dnyanopasak College, Parbhani 431 401, MS, India;
4.
d Department of Chemistry, Sharda Mahavidyalaya, Parbhani 431 401, MS, India

Corresponding author: Rajendra P. Pawar,
Received Date: 27 July 2013
Available Online: 29 November 2013

A simple, efficient, and environmentally benign method for the synthesis of 4H-chromene derivatives was developed using well ordered and recoverable amino functionalized silica gel as a base catalyst. The 4H-chromene derivatives were obtained in short time and excellent yield (87%-96%) by three component reaction of aldehydes, malononitrile and cyclic 1,3-diketones in water at 70 ℃.
- Aldehydes,
- 4H-Chromenes,
- Amino functionalized silica gel
1. [1]
  [1] G.J. Kelly, F. King, F. Kett, Waste elimination in condensation reactions of industrial importance, Green Chem. 4 (2002) 392-399.
2. [2]
  [2] J. Weitkamp, M. Hunger, U. Rymsa, Base catalysis on microporous and mesoporous materials: recent progress and perspectives, Microporous Mesoporous Mater. 48 (2001) 255-270.
3. [3]
  [3] R.A. Sheldon, Atom efficiency and catalysis in organic synthesis, Pure Appl. Chem. 72 (2000) 1233-1246.
4. [4]
  [4] A. Zapf, M. Beller, Fine chemical synthesis with homogeneous palladium catalysts: examples, status and trends, Top. Catal. 19 (2002) 101-109.
5. [5]
  [5] B.M. Choudary, M.L. Kantam, P. Sreekanth, et al., Knoevenagel and Aldol condensations catalysed by a new diamino-functionalised mesoporous material, J. Mol. Catal. A 142 (1999) 361-365.
6. [6]
  [6] Y. Kubota, Y. Nishizaki, H. Ikeya, et al., Organic silicate hybrid catalysts based on various defined structures for Knoevenagel condensation, Microporous Mesoporous Mater. 70 (2004) 135-149.
7. [7]
  [7] Y. Wan, D. Zhao, On the controllable soft-templating approach to mesoporous silicates, Chem. Rev. 107 (2007) 2821-2860.
8. [8]
  [8] Q.Q. Wang, D.F. Shantz, Ordered mesoporous silica-based inorganic nanocomposites, J. Solid State Chem. 181 (2008) 1659-1669.
9. [9]
  [9] X.G. Wang, K.S.K. Lin, J.C.C. Chan, S.F. Cheng, Direct synthesis and catalytic applications of ordered large pore aminopropyl-functionalized SBA-15 mesoporous materials, J. Phys. Chem. B 109 (2005) 1763-1769.
10. [10]
  [10] Y. Kubota, K. Goto, S. Miyata, et al., Enhanced effect of mesoporous silica on basecatalyzed Aldol reaction, Chem. Lett. 32 (2003) 234-235.
11. [11]
  [11] A.C. Blanc, D.J. Macquarrie, S. Valle, et al., The preparation and use of novel immobilised guanidine catalysts in base-catalysed epoxidation and condensation reactions, Green Chem. 2 (2000) 283-288.
12. [12]
  [12] X.G. Wang, Y.H. Tseng, J.C.C. Chan, S.F. Cheng, Catalytic applications of aminopropylated mesoporous silica prepared by a template-free route in flavanones, J. Catal. 233 (2005) 266-275.
13. [13]
  [13] M. Luechinger, A. Kienhofer, G.D. Pirngruber, Immobilized complexes of metals with amino acid ligands -a first step toward the development of new biomimetic catalysts, Chem. Mater. 18 (2006) 1330-1336.
14. [14]
  [14] D. Lu, Y. Li, Y. Gong, Organocatalytic asymmetric tandem Michael additionhemiacetalization: a route to chiral dihydrocoumarins, chromanes, and 4Hchromenes, J. Org. Chem. 75 (2010) 6900-6907.
15. [15]
  [15] W. Kemnitzer, J. Drewe, S. Jiang, et al., Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell and caspase-based high throughput screening assay. 4. Structure-activity relationships of N-alkyl substituted pyrrole fused at the 7,8-positions, J. Med. Chem. 51 (2008) 417-423.
16. [16]
  [16] E.C. Witte, P. Neubert, A. Roesch, 7-(Piperazinyl propoxy)-2H-1-benzopyran-2-ones, Ger. Offen DE, 3427985, Chem. Abstr. 104 (1986) 224915f.
17. [17]
  [17] J. Kuthan, Pyrans, thiopyrans, and selenopyrans, Adv. Heterocycl. Chem. 34 (1983) 145-157.
18. [18]
  [18] M. Suarez, E. Salfran, Y. Verdecia, et al., X-ray and theoretical structural study of novel 5,6,7,8-tetrahydrobenzo-4H-pyrans, Tetrahedron 58 (2002) 953-960.
19. [19]
  [19] A. Molla, E. Hossain, S. Hussain, Multicomponent domino reactions: borax catalyzed synthesis of highly functionalised pyran-annulated heterocycles, RSC Adv. 3 (2013) 21517-21523.
20. [20]
  [20] K. Niknam, A. Jamali, Silica-bonded N-propylpiperazine sodium n-propionate as recyclable basic catalyst for synthesis of 3,4-dihydropyrano[c]chromene derivatives and biscoumarins, Chin. J. Catal. 33 (2012) 1840-1849.
21. [21]
  [21] S. Paul, P. Bhattacharyya, A.R. Das, One-pot synthesis of dihydropyrano[2,3-c]chromenes via a three component coupling of aromatic aldehydes, malononitrile, and 3-hydroxycoumarin catalyzed by nano-structured ZnO in water: a green protocol, Tetrahedron Lett. 52 (2011) 4636-4641.
22. [22]
  [22] N. Martin, C. Pascual, C. Seoane, J.L. Soto, The use of some activated nitriles in heterocyclic syntheses, Heterocycles 26 (1987) 2811-2816.
23. [23]
  [23] A.F. Harb, A.M. Hesien, S.A. Metwally, M.H. Elnagdi, The reaction of ethyl 6-amino-5-cyano-4-aryl-2-methyl-4H-pyran-3-carboxylate with nucleophilic reagents, Ann. Chem. (1989) 585-590.
24. [24]
  [24] S.E. Zayed, E.I. Abou-Elmaged, S.A. Metwally, M.H. Elnagdi, Reactions of sixmembered heterocyclic β-enaminonitriles with electrophilic reagents, Chem. Commun. 56 (1991) 2175-2182.
25. [25]
  [25] I. Devi, P.J. Bhuyan, Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions, Tetrahedron Lett. 45 (2004) 8625-8627.
26. [26]
  [26] X.S. Wang, D.Q. Shi, S.J. Tu, C.S. Yao, A convenient synthesis of 5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran derivatives catalyzed by KF-alumina, Syn. Commun. 33 (2003) 119-126.
27. [27]
  [27] V. Manu, H.M. Mody, H.C. Bajaj, R.V. Jasra, Adsorption of Cu²⁺ on amino functionalized silica gel with different loading, Ind. Eng. Chem. Res. 48 (2009) 8954-8960.
28. [28]
  [28] R.L. Magar, P.B. Thorat, V.B. Jadhav, et al., Silica gel supported polyamine: a versatile catalyst for one pot synthesis of 2-amino-4H-chromene derivatives, J. Mol. Catal. A: Chem. 374-375 (2013) 118-124.
1. [1]
  Lei Shen , Yang Zhang , Linlin Zhang , Chuanwang Liu , Zhixian Ma , Kangjiang Liang , Chengfeng Xia . Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes. Chinese Chemical Letters, 2024, 35(4): 108742-. doi: 10.1016/j.cclet.2023.108742
2. [2]
  Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
3. [3]
  Zhikang Wu , Guoyong Dai , Qi Li , Zheyu Wei , Shi Ru , Jianda Li , Hongli Jia , Dejin Zang , Mirjana Čolović , Yongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061
4. [4]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
5. [5]
  Jinyuan Cui , Tingting Yang , Teng Xu , Jin Lin , Kunlong Liu , Pengxin Liu . Hydrogen spillover enhances the selective hydrogenation of α,β-unsaturated aldehydes on the Cu-O-Ce interface. Chinese Journal of Structural Chemistry, 2025, 44(1): 100438-100438. doi: 10.1016/j.cjsc.2024.100438
6. [6]
  Tong Zhang , Xiaojing Liang , Licheng Wang , Shuai Wang , Xiaoxiao Liu , Yong Guo . An ionic liquid assisted hydrogel functionalized silica stationary phase for mixed-mode liquid chromatography. Chinese Chemical Letters, 2025, 36(1): 109889-. doi: 10.1016/j.cclet.2024.109889
7. [7]
  Mengjun Sun , Zhi Wang , Jvhui Jiang , Xiaobing Wang , Chuang Yu . Gelation mechanisms of gel polymer electrolytes for zinc-based batteries. Chinese Chemical Letters, 2024, 35(5): 109393-. doi: 10.1016/j.cclet.2023.109393
8. [8]
  Gang Hu , Chun Wang , Qinqin Wang , Mingyuan Zhu , Lihua Kang . The controlled oxidation states of the H₄PMo₁₁VO₄₀ catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298
9. [9]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
10. [10]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
11. [11]
  Sikai Wu , Xuefei Wang , Huogen Yu . Hydroxyl-enriched hydrous tin dioxide-coated BiVO4 with boosted photocatalytic H2O2 production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100457-100457. doi: 10.1016/j.cjsc.2024.100457
12. [12]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
13. [13]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
14. [14]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
15. [15]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
16. [16]
  Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H₂O₂ Production and Cr(VI) Reduction over a Hierarchical Ti₃C₂/In₄SnS₈ Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
17. [17]
  Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
18. [18]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
19. [19]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
20. [20]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(626)
HTML views(26)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142