One-pot three-component Mannich reaction catalyzed by sucrose char sulfonic acid

doi:10.1007/s11705-009-0052-5

Front Chem Eng Chin

2009, Vol. 3

Issue (2) : 201-205 https://doi.org/10.1007/s11705-009-0052-5

RESEARCH ARTICLE

One-pot three-component Mannich reaction catalyzed by sucrose char sulfonic acid

Qiong XU, Zhigao YANG, Dulin YIN(

), Jihui WANG

Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Institute of Fine Catalysis and Synthesis, Hunan Normal University, Changsha 410081, China

Download: PDF(119 KB) HTML
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract

Sucrose char sulfonic acid efficiently catalyzed the one-pot three-component Mannich reaction of ketones, aromatic aldehydes and amines in ethanol to afford the corresponding b-amino carbonyl compounds in good to excellent yields. A series of heteroaromatic b-amino carbonyl compounds can be obtained when using 2-acetylpyrazine as substrate. This reaction can be performed under mild reaction conditions with clean reaction profiles and a simple workup procedure.

Keywords One–pot synthesis b-amino ketone char sulfonic acid 2-acetylpyrazine catalysis

Corresponding Author(s): YIN Dulin,Email:dulinyin@126.com

Issue Date: 05 June 2009

Cite this article:

Qiong XU,Zhigao YANG,Dulin YIN, et al. One-pot three-component Mannich reaction catalyzed by sucrose char sulfonic acid[J]. Front Chem Eng Chin, 2009, 3(2): 201-205.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-009-0052-5
https://academic.hep.com.cn/fcse/EN/Y2009/V3/I2/201

Fig.1 One-pot three-component Mannich reaction of aromatic aldehydes, aromatic amines and ketones in heterogenous acidic catalytic system

Tab.1 One-pot three-component Mannich reaction catalyzed by sucrose char sulfonic acid

1	Kobayashi S, Ishitani H. Catalytic enantioselective addition to imines. Chem Rev , 1999, 99: 1069-1094 doi: 10.1021/cr980414z
2	Speckamp W N, Moolenaar M J. New developments in the chemistry of N-acyliminium ions and related intermediates. Tetrahedron , 2000, 56: 3817-3856 doi: 10.1016/S0040-4020(00)00159-9
3	Bur S K, Martin S F. Vinylogous Mannich reactions: selectivity and synthetic utility. Tetrahedron , 2001, 57: 3221-3242 doi: 10.1016/S0040-4020(01)00035-7
4	Coardova A. The direct catalytic asymmetric Mannich reaction. Acc Chem Res , 2004, 37: 102-112 doi: 10.1021/ar030231l
5	Davis F A, Zhang Y, Anilkumar G. Asymmetric synthesis of the quinolizidine alkaloid (–)-epimyrtine with intramolecular Mannich cyclization and N-sulfinyl δ-amino-β-ketoesters. J Org Chem , 2003, 68: 8061-8064 doi: 10.1021/jo030208d
6	Evans G B, Furneaux R H, Tyler P C. Synthesis of a transition state analogue inhibitor of purine nucleoside phosphorylase via the Mannich reaction. Org Lett , 2003, 5: 3639-3640 doi: 10.1021/ol035293q
7	Rivera A, Quevedo R. Solvent-free Mannich-type reaction as a strategy for synthesizing novel heterocalixarenes. Tetrahedron Lett , 2004, 45: 8335-8338 doi: 10.1016/j.tetlet.2004.09.066
8	Prukala D. New compounds via Mannich reaction of cytosine, paraformaldehyde and cyclic secondary amines. Tetrahedron Lett , 2006, 47: 9045-9047 doi: 10.1016/j.tetlet.2006.10.117
9	Córdova A, Barbas III C F. anti-Selective SMP-catalyzed direct asymmetric Mannich-type reactions: synthesis of functionalized amino acid derivatives. Tetrahedron Lett , 2002, 43: 7749-7752 doi: 10.1016/S0040-4039(02)01772-0
10	Cooke A, Bennett J, McDaid E. A facile synthesis of N-benzyl-4-acetylproline via a tandem cationic aza-Cope rearrangement-Mannich reaction. Tetrahedron Lett , 2002, 43: 903-905 doi: 10.1016/S0040-4039(01)02287-0
11	Chen S L, Ji S J, Loh T P. Asymmetric Mannich-type reactions catalyzed by indium(III) complexes in ionic liquids. Tetrahedron Lett , 2003, 44: 2405-2408 doi: 10.1016/S0040-4039(03)00189-8
12	Trost B M, Terrell L R. A direct catalytic asymmetric Mannich-type reaction to synamino alcohols. J Am Chem Soc , 2003, 125: 338-339 doi: 10.1021/ja028782e
13	Shibasaki M. Kumagai N, Harada S. anti-Selective direct catalytic asymmetric Mannich-type reaction of hydroxyketone providing β-amino alcohols. J Am Chem Soc , 2003, 125: 4712-4713 doi: 10.1021/ja034787f
14	Tremblay-Morin J P, Raeppel S, Gaudette F. Lewis acid-catalyzed Mannich type reactions with potassium organotrifluoroborates. Tetrahedron Lett , 2004, 45: 3471-3474 doi: 10.1016/j.tetlet.2004.03.014
15	Ollevier T, Nadeau E. Bismuth triflate-catalyzed three-component Mannich-type reaction. J Org Chem , 2004, 69: 9292-9295 doi: 10.1021/jo048617c
16	Josephsohn N S, Carswell E L, Snapper M L, Hoveyda A H. Practical and highly enantioselective synthesis of β-alkynyl-β-amino esters through Ag-catalyzed asymmetric Mannich reactions of silylketene acetals and alkynyl imines. Org Lett , 2005, 7: 2711-2713 doi: 10.1021/ol050910r
17	Urbaniak M, Iwanek W. Synthesis of alkoxymethyl derivatives of resorcinarene via the Mannich reaction catalysed with iminodiacetic acid. Tetrahedron , 2006, 62: 1508-1511 doi: 10.1016/j.tet.2005.11.017
18	Hasegawa A, Naganawa Y, Fushimi M, Ishihara K, Yamamoto H. Design of Br?nsted acid-assisted chiral Br?nsted acid catalyst bearing a bis(triflyl)methyl group for a Mannich-type reaction. Org Lett , 2006, 8: 3175-3178 doi: 10.1021/ol060939a
19	Yi W B, Cai Ch. Mannich-type reactions of aromatic aldehydes, anilines, and methyl ketones in fluorous biphase systems created by rare earth (III) perfluorooctane sulfonates catalysts in fluorous media. J Fluorine Chem , 2006, 127: 1515-1521 doi: 10.1016/j.jfluchem.2006.07.009
20	Fang D, Luo J, Zhou X L, Liu Z L. Mannich reaction in water using acidic ionic liquid as recoverable and reusable catalyst. Catal Lett , 2007, 116: 76-80 doi: 10.1007/s10562-007-9095-8
21	Yang D Ch, Zhang G L, Yang Y, Zhong Y G. The Mannich reaction of 4-methylacetophenone with aromatic aldehydes and aromatic amines. Chem J Chin Univ , 2000, 21: 1694-1696
22	Hayashi Y, Tsuboi W, Shoji M, Suzuki N. Application of high pressure induced by water-freezing to the direct catalytic asymmetric three-component list-barbas-Mannich reaction. J Am Chem Soc , 2003, 125: 11208-11209 doi: 10.1021/ja0372513
23	Joshi N S, Whitaker L R, Francis M B. A three-component Mannich-type reaction for selective tyrosine bioconjugation. J Am Chem Soc , 2004, 126: 15942-15943 doi: 10.1021/ja0439017
24	Pandey G, Singh R P, Garg A, Singh V K. Synthesis of Mannich type products via a three-component coupling reaction. Tetrahedron Lett , 2005, 46: 2137-2140 doi: 10.1016/j.tetlet.2005.01.118
25	Ollevier T, Nadeau E, Guay-Begin A. Direct-type catalytic three-component Mannich reaction in aqueous media. Tetrahedron Lett , 2006, 47: 8351-8354 doi: 10.1016/j.tetlet.2006.09.082
26	Azizi N, Torkiyan L, Saidi M R. Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids. Org Lett , 2006, 8: 2079-2082 doi: 10.1021/ol060498v
27	Hirose T, Sunazuka T, Yamamoto D, Kaji E, Omura S. Synthetic applications of a three-component Mannich reaction. Total synthesis of IL-6 inhibitor (+)-madindoline A and B. Tetrahedron Lett , 2006, 47: 6761-6764 doi: 10.1016/j.tetlet.2006.07.083
28	Wu M, Jing H W, Chang T. Synthesis of β-amino carbonyl compounds via a Mannich reaction catalyzed by SalenZn complex. Catal Commun , 2007, 8: 2217-2221 doi: 10.1016/j.catcom.2007.05.011
29	Harmer M A, Sun Q. Solid acid catalysis using ion-exchange resins. Appl Catal A , 2001, 221: 45-62 doi: 10.1016/S0926-860X(01)00794-3
30	Xu Y J, Gu W Q, Gin D L. Heterogeneous catalysis using a nanostructured solid acid resin based on lyotropic liquid crystals. J Am Chem Soc , 2004, 126: 1616-1617 doi: 10.1021/ja038501i
31	Yang L M, Wang Y J, Luo G S, Dai Y Y. Functionalization of SBA-15 mesoporous silica with thiol or sulfonic acid groups under the crystallization conditions. Micro Meso Mater , 2005, 84: 275-282 doi: 10.1016/j.micromeso.2005.05.037
32	Palaniappan S, John A. A novel polyaniline-fluoroboric acid-dodecylhydrogensulfate salt: versatile reusable polymer based solid acid catalyst for organic transformations. J Mol Catal A , 2005, 233: 9-15 doi: 10.1016/j.molcata.2005.02.002
33	Bigdeli M A, Nemati F, Mahdavinia G H. HClO₄-SiO₂ catalyzed stereoselective synthesis of β-amino ketones via a direct Mannich-type reaction. Tetrahedron Lett , 2007, 48: 6801-6804 doi: 10.1016/j.tetlet.2007.07.088
34	Xu Q, Yang Z G, Yin D L, Zhang F. Synthesis of chalcones catalyzed by a novel solid sulfonic acid from bamboo. Catal Commun , 2008, 9: 1579-1582 doi: 10.1016/j.catcom.2008.01.007

[1]	Ling Tan, Kipkorir Peter, Jing Ren, Baoyang Du, Xiaojie Hao, Yufei Zhao, Yu-Fei Song. Photocatalytic syngas synthesis from CO₂ and H₂O using ultrafine CeO₂-decorated layered double hydroxide nanosheets under visible-light up to 600 nm[J]. Front. Chem. Sci. Eng., 2021, 15(1): 99-108.
[2]	Qingzhuo Ni, Hao Cheng, Jianfeng Ma, Yong Kong, Sridhar Komarneni. Efficient degradation of orange II by ZnMn₂O₄ in a novel photo-chemical catalysis system[J]. Front. Chem. Sci. Eng., 2020, 14(6): 956-966.
[3]	Baoyu Liu, Qiaowen Mu, Jiajin Huang, Wei Tan, Jing Xiao. Fabrication of titanosilicate pillared MFI zeolites with tailored catalytic activity[J]. Front. Chem. Sci. Eng., 2020, 14(5): 772-782.
[4]	Cyrine Ayed, Wei Huang, Kai A. I. Zhang. Covalent triazine framework with efficient photocatalytic activity in aqueous and solid media[J]. Front. Chem. Sci. Eng., 2020, 14(3): 397-404.
[5]	Tingting Zhao, Niamat Ullah, Yajun Hui, Zhenhua Li. Review of plasma-assisted reactions and potential applications for modification of metal–organic frameworks[J]. Front. Chem. Sci. Eng., 2019, 13(3): 444-457.
[6]	Kadriye Özlem Hamaloğlu, Ebru Sağ, Çiğdem Kip, Erhan Şenlik, Berna Saraçoğlu Kaya, Ali Tuncel. Magnetic-porous microspheres with synergistic catalytic activity of small-sized gold nanoparticles and titania matrix[J]. Front. Chem. Sci. Eng., 2019, 13(3): 574-585.
[7]	Anandarup Goswami, Manoj B. Gawande. Phosphorene: Current status, challenges and opportunities[J]. Front. Chem. Sci. Eng., 2019, 13(2): 296-309.
[8]	J. Christopher Whitehead. Plasma-catalysis: Is it just a question of scale?[J]. Front. Chem. Sci. Eng., 2019, 13(2): 264-273.
[9]	Andrea P. Reverberi, P.S. Varbanov, M. Vocciante, B. Fabiano. Bismuth oxide-related photocatalysts in green nanotechnology: A critical analysis[J]. Front. Chem. Sci. Eng., 2018, 12(4): 878-892.
[10]	Yan Zhang, Jian Xiao, Qiying Lv, Shuai Wang. Self-supported transition metal phosphide based electrodes as high-efficient water splitting cathodes[J]. Front. Chem. Sci. Eng., 2018, 12(3): 494-508.
[11]	Dong Yang, Xiaoyan Zou, Yuanyuan Sun, Zhenwei Tong, Zhongyi Jiang. Fabrication of three-dimensional porous La-doped SrTiO₃ microspheres with enhanced visible light catalytic activity for Cr(VI) reduction[J]. Front. Chem. Sci. Eng., 2018, 12(3): 440-449.
[12]	Dongxu Han, Zhiguo Zhang, Zongbi Bao, Huabin Xing, Qilong Ren. Pd-Ni nanoparticles supported on titanium oxide as effective catalysts for Suzuki-Miyaura coupling reactions[J]. Front. Chem. Sci. Eng., 2018, 12(1): 24-31.
[13]	Jian Zhou, Zhicheng Liu, Yangdong Wang, Dejin Kong, Zaiku Xie. Shape selective catalysis in methylation of toluene: Development, challenges and perspectives[J]. Front. Chem. Sci. Eng., 2018, 12(1): 103-112.
[14]	Cunyao Li, Wenlong Wang, Li Yan, Yunjie Ding. A mini review on strategies for heterogenization of rhodium-based hydroformylation catalysts[J]. Front. Chem. Sci. Eng., 2018, 12(1): 113-123.
[15]	Yinlong Hu,Shuang Zheng,Fumin Zhang. Fabrication of MIL-100(Fe)@SiO₂@Fe₃O₄ core-shell microspheres as a magnetically recyclable solid acidic catalyst for the acetalization of benzaldehyde and glycol[J]. Front. Chem. Sci. Eng., 2016, 10(4): 534-541.

Viewed

Full text

Abstract

Cited

Shared

Discussed