European Journal of Chemistry

A simple, solvent and catalyst-free green synthetic protocol for α-amino phosphonates

Article Sidebar

PDF
Published: Mar 31, 2012
DOI: https://doi.org/10.5155/eurjchem.3.1.119-124.449
Keywords:
Amines, Solvent-free, Neat condition, Aromatic aldehydes, Multi component reaction, Trimethyl/triethyl phosphite
Section
Short Communication
Issue
Vol. 3 No. 1 (2012): March 2012
Dates
Received 2011-04-30
Accepted 2011-05-25
Published 2012-03-31


Main Article Content

Ramesh Katla
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500607, India
Narayana Murthy Sabbavarapu
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500607, India
Karnakar Konkala
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500607, India
Nageswar Yadavalli Venkata Durga
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500607, India

Abstract

A simple and efficient method for the synthesis of α-amino phosphonates has been developed by using aromatic aldehydes, amines, and trimethyl/triethyl phosphite, under catalyst and solvent free conditions, with the formation of the product in good to excellent yields. This method involves milder reaction conditions, easy work-up, and cleaner reaction profiles, and may have wide spread application in organic synthesis.

3_1_119_124_800


icon graph This Abstract was viewed 2302 times | icon graph Article PDF downloaded 919 times

How to Cite
(1)
Katla, R.; Sabbavarapu, N. M.; Konkala, K.; Durga, N. Y. V. A Simple, Solvent and Catalyst-Free Green Synthetic Protocol for α-Amino Phosphonates. Eur. J. Chem. 2012, 3, 119-124.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Allen, M. C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J. M. J Med. Chem. 1989, 32, 1652-1661.
http://dx.doi.org/10.1021/jm00127a041
PMid:2661820

[2]. Peyman, A.; Stahl, W.; Wagner, K.; Ruppert, D.; Budt, K. H. Bioorg. Med. Chem. Lett. 1994, 4, 2601-2604.
http://dx.doi.org/10.1016/S0960-894X(01)80292-4

[3]. Atherton, F. R.; Hassal, C. H.; Lambert, R. W. J. Med. Chem. 1986, 29, 29-40.
http://dx.doi.org/10.1021/jm00151a005
PMid:3510298

[4]. Maier, L.; Spoerri, H. Phosphorus, Sulfur, Silicon Relat Elem. 1991, 61, 69-75.
http://dx.doi.org/10.1080/10426509108027339

[5]. Emsley, J.; Hall, D. In: The Chemistry of Phosphorous; Harper & Row: London, 1976, p. 494.

[6]. Meyer, J. H.; Barlett, P. A. J. Am. Chem. Soc. 1998, 120, 4600-4609.
http://dx.doi.org/10.1021/ja973715j

[7]. Miller, D. J.; Hammond, S. M.; Anderluzzi, D.; Bugg, T. D. H. J. Chem. Soc., Perkin Trans. 1998, 1, 131-142.

[8]. Manabe, K.; Kobayashi, S. Chem. Commun. 2000, 8, 669-670.
http://dx.doi.org/10.1039/b000319k

[9]. Xu, F.; Luo, Y.; Deng, M.; Shen, Q. Eur. J. Org. Chem. 2003, 35(15), 4728-4730.
http://dx.doi.org/10.1002/ejoc.200300545

[10]. Ranu, B. C.; Hajra, A.; Jana, J. Org. Lett. 1999, 1, 1141-1143.
http://dx.doi.org/10.1021/ol990079g

[11]. Chandrasekhar, S.; Jaya Prakash, S.; Jagadeshwar, V.; Narsihmula, C. Tetrahedron Lett. 2001, 42, 5561-5563.
http://dx.doi.org/10.1016/S0040-4039(01)01053-X

[12]. Kudrimoti, S.; Rao, V. B. Tetrahedron Lett. 2005, 46, 1209-1210.
http://dx.doi.org/10.1016/j.tetlet.2004.12.070

[13]. Heydari, A.; Zarei, M.; Alijanianzadeh, R.; Tavakol, H. Tetrahedron Lett. 2001, 42, 3629-3631.
http://dx.doi.org/10.1016/S0040-4039(01)00233-7

[14]. Yadav, J. S.; Reddy, B. V. S.; Madan, C. Synlett. 2001, 7, 1131-1133.
http://dx.doi.org/10.1055/s-2001-15162

[15]. Yadav, J. S.; Reddy, B. V. S.; Raj, S.; Reddy, K. B.; Prasad, A. R. Synthesis 2001, 15, 2277-2280.
http://dx.doi.org/10.1055/s-2001-18444

[16]. Kaboudin, B.; Nazari, R. Tetrahedron Lett. 2001, 42, 8211-8213.
http://dx.doi.org/10.1016/S0040-4039(01)01627-6

[17]. Yadav, J. S.; Reddy, B. V. S.; Sreedhar, P. Green Chem. 2002, 4, 436-438.
http://dx.doi.org/10.1039/b203934f

[18]. Heydari, A.; Hamedi, H.; Pourayoubi, M. Catal. Commun. 2007, 8, 1224-1226.
http://dx.doi.org/10.1016/j.catcom.2006.11.008

[19]. Vahdat, S. M.; Baharfar, R.; Tajbakhsh, M.; Heydari, A.; Baghbanian, S. M.; Khaksar, S. Tetrahedron Lett. 2008, 49, 6501-6504.
http://dx.doi.org/10.1016/j.tetlet.2008.08.094

[20]. Hosseini-Sarvari, M. Tetrahedron 2008, 64, 5459-5466.
http://dx.doi.org/10.1016/j.tet.2008.04.016

[21]. Perumal, P. T.; Thirumurugan, P.; Kumar, A. N.; Sudha Priya, N.; Muralidaran, D. Tetrahedron Lett. 2010, 51, 5708-5712.
http://dx.doi.org/10.1016/j.tetlet.2010.08.066

[22]. Bhattacharya, A. K.; Rana, C. K. Tetrahedron Lett. 2008, 49, 2598-2601.
http://dx.doi.org/10.1016/j.tetlet.2008.02.102

[23]. Heydari, A.; Arefi, A. Catal. Commun. 2007, 8, 1023-1026.
http://dx.doi.org/10.1016/j.catcom.2006.10.019

[24]. Qian, C.; Huang, T. J. Org. Chem. 1998, 63, 4125-4128.
http://dx.doi.org/10.1021/jo971242t

[25]. Ghosh, R.; Maiti, S.; Chakraborty, A.; Maiti, D. A. J. Mol. Catal. A: Chem. 2004, 210, 53-57.
http://dx.doi.org/10.1016/j.molcata.2003.09.020

[26]. Bhagat, S.; Chakraborti, A. K. J. Org. Chem. 2007, 72, 1263-1270.
http://dx.doi.org/10.1021/jo062140i
PMid:17253748

[27]. Murthy, S. N.; Madhav, B.; Reddy, V. P.; Nageswar, Y. V. D. Tetrahedron Lett. 2010, 51, 3649-3653.
http://dx.doi.org/10.1016/j.tetlet.2010.05.028

[28]. Shankar, J.; Karnakar, K.; Srinivas, B.; Nageswar, Y. V. D. Tetrahedron Lett. 2010, 51, 3938-3939.
http://dx.doi.org/10.1016/j.tetlet.2010.05.096

[29]. Rao, K. R.; Nageswar, Y. V. D.; Srilaxmi, K.; Surendra, K. Advances in Organic Synthesis, Vol. 1, Bentham Science Publishers Ltd. 2005, 301-339.

[30]. Murthy, S. N.; Madhav, B.; Kumar, A. V.; Rao, K. R.; Nageswar, Y. V. D. Tetrahedron. 2009, 65, 5251-5256.
http://dx.doi.org/10.1016/j.tet.2009.04.081

[31]. Murthy, S. N.; Madhav, B.; Kumar, A. V.; Rao, K. R.; Nageswar, Y. V. D. Helvetica Chim. Acta 2009, 92, 2118-2124.
http://dx.doi.org/10.1002/hlca.200900098

Supporting Agencies

Council of Scientific and Industrial Research, New Delhi
Most read articles by the same author(s)

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).