European Journal of Chemistry

One-pot multicomponent route to propargylamines using ferric hydrogensulfate



Main Article Content

Hossein Eshghi
Gholam Hossein Zohuri
Saman Damavandi

Abstract

The one-pot three-component coupling reaction of phenylacetylene, aldehyde and amine derivatives in the presence of ferric hydrogensulfate, [(Fe(HSO4)3], as an efficient heterogeneous catalyst is reported. The catalyst displayed high activity and afforded the corresponding propargylamines in good to excellent yields. This method provides the wide range of substrate applicability. Heterogeneous nature of the catalyst made it reusable for further chemical reactions.

2_1_100_103_800


icon graph This Abstract was viewed 7535 times | icon graph Article PDF downloaded 939 times

How to Cite
(1)
Eshghi, H.; Zohuri, G. H.; Damavandi, S. One-Pot Multicomponent Route to Propargylamines Using Ferric Hydrogensulfate. Eur. J. Chem. 2011, 2, 100-103.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. McMurry, J. Organic Chemistry, Brooks/Cole, Pacific Grove, CA, 2000.

[2]. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Kluwer Academic/Plenum, New York, 2000.

[3]. Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem. 1999, 71, 1407-1415.
doi:10.1351/pac199971081407

[4]. Goldfuss B. Topics in Organometallic Chemistry, eds. Brown, J. M.; Dixneuf, P.; Fürstner, A.; Hegedus, L. S.; Hofmann, P.; Knochel, P.; Koten G. V.; Murai, S.; Reetz, M. Springer, Heidelberg, 2003.

[5]. Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
doi:10.1021/cr940474e
PMid:11848938

[6]. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094.
doi:10.1021/cr980414z
PMid:11749440

[7]. Ellman, J. A.; Owens, T. D.; Tang, T.P. Acc. Chem. Res. 2002, 35, 984-995.
doi:10.1021/ar020066u
PMid:12437323

[8]. Legros, J.; Meyer, F.; Coliboeuf M.; Crousse, B.; Bonnet-Delpon, D.; Begue, J. P. J. Org. Chem. 2003, 68, 6444-6446.
doi:10.1021/jo034205c
PMid:12895086

[9]. Akullian, L. C.; Snapper, M. L.; Hoveyda, A.H. Angew. Chem. Int. Ed. Engl. 2003, 42, 4244-4247.
doi:10.1002/anie.200352081
PMid:14502747

[10]. Traverse, J. F., Hoveyda, A. H.; Snapper, M. L. Org. Lett. 2003, 5, 3273-3275.
doi:10.1021/ol035138b
PMid:12943405

[11]. Prajapati, D.; Laskar, D. D.; Gogoi B. J.; Devi, G. Tetrahedron Lett. 2003, 44, 6755-6757.
doi:10.1016/S0040-4039(03)01640-X

[12]. Mori, Y.; Hayashi, H. Tetrahedron 2002, 58, 1789-1797.
doi:10.1016/S0040-4020(02)00038-8

[13]. Galliford, C. V.; Beenen, M. A.; Nguyen, S. T.; Scheidt, K. A. Org. Lett. 2003, 5, 3487-3490.
doi:10.1021/ol035292y
PMid:12967306

[14]. Garcia, C. I.; Tillack, A.; Hartung, C. G.; Beller, M. Tetrahedron Lett. 2003, 44, 3217-3221.
doi:10.1016/S0040-4039(03)00448-9

[15]. Takahashi, T.; Bao, F.; Gao, G.; Ogasawara, M. Org. Lett, 2003, 5, 3479-34814.
doi:10.1021/ol035277t
PMid:12967304

[16]. Qian, M.; Negishi, E. Org. Proc. Res. Dev. 2003, 7, 412-421.
doi:10.1021/op034029+

[17]. Umeno, M.; Suzuki, A. Handbook of Grignard Reagent, Eds. Silverman, G. S.; Rakita, P. E., Dekker, New York, 1996, 64, 645-450.

[18]. Tuulmets, A.; Pallin, V.; Tammiku-Taul, J.; Burk, P.; Raie, K. J Phys. Org. Chem. 2002, 15, 701-705.
doi:10.1002/poc.534

[19]. Harada, T.; Fujiwara, T.; Iwazaki K.; Oku A. Org. Lett. 2000, 2, 1855-1857.
doi:10.1021/ol0059145
PMid:10891175

[20]. Rosas, N.; Sharma, P.; Alvarez, C.; Gomez, E.; Gutierrez, Y.; Mendez, M.; Toscano, R. A.; Maldonado, L. A. Tetrahedron Lett. 2003, 44, 8019-8022.
doi:10.1016/j.tetlet.2003.08.104

[21]. Miyamoto, H.; Daikawa, N.; Tanaka, K. Tetrahedron Lett. 2003, 44, 6963-6964.
doi:10.1016/S0040-4039(03)01649-6

[22]. Manabe, K.; Kobayashi S. Chem. Eur. J., 2002, 8, 4094-4101.
doi:10.1002/1521-3765(20020916)8:18<4094::AID-CHEM4094>3.0.CO;2-G

[23]. Dyker, G. Angew. Chem. 1999, 38, 1698-1712.
doi:10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO;2-6

[24]. Wang M.; Li, P.; Wang, L. Eur. J. Org. Chem. 2008, 13, 2255-2261.
doi:10.1002/ejoc.200800006

[25]. Patil, M. K.; Keller, M.; Reddy, B. M.; Pale, P.; Sommer, J. Eur. J. Org. Chem. 2008, 26, 4440-4445.
doi:10.1002/ejoc.200800359

[26]. Leadbeater, N. E.; Torenius, H. M.; Tye, H. Mol. Div 2003, 7, 135-144.
doi:10.1023/B:MODI.0000006822.51884.e6
PMid:14870842

[27]. Li, C-J. Acc. Chem. Res. 2010, 43, 581-590.
doi:10.1021/ar9002587
PMid:20095650

[28]. Sugiishi, T.; Kimura A.; Nakamura H. J. Am. Chem. Soc. 2010, 132, 5332–5333.
doi:10.1021/ja9109055
PMid:20353176

[29]. Nakamura, S.; Ohara, M.; Nakamura, Y.; Shibata, N.; Toru T. Chem. Eur. J. 2010, 16, 2360-2362.
doi:10.1002/chem.200903550
PMid:20108286

[30]. Wei, C.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584-9585.
doi:10.1021/ja0359299
PMid:12904013

[31]. Li, Z.; Wei, C.;. Chen L; Varma, R. S.; Li, C. J. Tetrahedron Lett. 2004, 45, 2443-2446.
doi:10.1016/j.tetlet.2004.01.044

[32]. Shi, L.; Tu, Y. Q.; Wang, M.; Zhang, F. M.; Fan, C. A. Org. Lett. 2004, 6, 1001-1003.
doi:10.1021/ol049936t
PMid:15012085

[33]. Eshghi, H. J. Chin. Chem. Soc. 2006, 53, 987-990.

[34]. Eshghi, H.; Rahimizadeh, M.; Saberi, S. Catal. Commun. 2008, 9, 2460-2466.
doi:10.1016/j.catcom.2008.06.015

[35]. Kantam, M. L.; Balasubrahmanyam, V.; Kumar, K. B. S.; Venkanna, G. T. Tetrahedron Lett. 2007, 48, 7332-7334.
doi:10.1016/j.tetlet.2007.08.020

[36]. Kidwai, M.; Bansal, V.; Kumarb, A.; Mozumdar, S. Green Chem. 2007, 9, 742-745.
doi:10.1039/b702287e

[37]. Vanessa, K. Y. L.; Yungen, L.; Man-Kin, W.; Chi-Ming, C. Org. Lett. 2006, 8, 8-11.

[38]. Wei, C.; Li, Z.; Li, C.J. Org. Lett. 2003, 5, 23-26.
doi:10.1021/ol035781y
PMid:14602028

[39]. Park, S. B.; Alper, H. Chem. Commun. 2005, 1315-1317.
doi:10.1039/b416268d
PMid:15742063

[40]. Yadav, J. S.; Reddy, B. V. S.; Gopal, A. V. H.; Patil, K. S. Tetrahedron Lett. 2009, 50, 3493-3495.
doi:10.1016/j.tetlet.2009.03.014

[41]. Kantam, M.; Laha, S.; Yadav, J.; Bhargava, S. Tetrahedron Lett. 2008, 49, 3083–3086.
doi:10.1016/j.tetlet.2008.03.053

[42]. Reddy, K. M.; Seshu, B. N.; Suryanarayana, I.; Prasad, P. S.; Lingaiah, N. Tetrahedron Lett. 2006, 47, 7563-7566.
doi:10.1016/j.tetlet.2006.08.094

[43]. Samai, S.; Chandra, N. G.; Singh, M. S. Tetrahedron Lett. 2010, 51, 5555-5558.
doi:10.1016/j.tetlet.2010.08.043

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).