European Journal of Chemistry 2012, 3(1), 119-124. doi:https://doi.org/10.5155/eurjchem.3.1.119-124.449

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


Ramesh Katla (1) , Narayana Murthy Sabbavarapu (2) , Karnakar Konkala (3) , Nageswar Yadavalli Venkata Durga (4,*)

(1) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500607, India
(2) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500607, India
(3) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500607, India
(4) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500607, India
(*) Corresponding Author

Received: 30 Apr 2011, Accepted: 25 May 2011, Published: 31 Mar 2012

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


Keywords


Amines; Solvent-free; Neat condition; Aromatic aldehydes; Multi component reaction; Trimethyl/triethyl phosphite

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.3.1.119-124.449

Article Metrics


This Abstract was viewed 880 times | PDF Article downloaded 287 times

Citations

/


[1]. Hashem Sharghi, Sakineh Ebrahimpourmoghaddam, Mohammad Mahdi Doroodmand
Iron-doped single walled carbon nanotubes as an efficient and reusable heterogeneous catalyst for the synthesis of organophosphorus compounds under solvent-free conditions
Tetrahedron  69(23), 4708, 2013
DOI: 10.1016/j.tet.2013.03.073
/


[2]. Hongjun Wang, Tao Deng, Chun Cai
Fluorous bis(oxazolines) ligand: Synthesis and application in Kabachnik-Fields reaction
Journal of Fluorine Chemistry  168, 144, 2014
DOI: 10.1016/j.jfluchem.2014.09.024
/


[3]. Mario Ordóñez, José Luis Viveros-Ceballos, Carlos Cativiela, Francisco J. Sayago
An update on the stereoselective synthesis of α-aminophosphonic acids and derivatives
Tetrahedron  71(12), 1745, 2015
DOI: 10.1016/j.tet.2015.01.029
/


[4]. Mohd Nazish, S. Saravanan, Noor-ul H. Khan, Prathibha Kumari, Rukhsana I. Kureshy, Sayed H. R. Abdi, Hari C. Bajaj
Magnetic Fe3O4Nanoparticle-Supported Phosphotungstic Acid as a Recyclable Catalyst for the Kabachnik-Fields Reaction of Isatins, Imines, and Aldehydes under Solvent-Free Conditions
ChemPlusChem  , n/a, 2014
DOI: 10.1002/cplu.201402191
/


[5]. Jilla Shankar, Gaddam Satish, Bandam Santosh Pavan Anil Kumar, Yadavalli Venkata Durga Nageswar
β-Cyclodextrin catalyzed synthesis of substituted indoles in aqueous medium
European Journal of Chemistry  5(4), 668, 2014
DOI: 10.5155/eurjchem.5.4.668-670.1085
/


[6]. Jilla Shankar, Gaddam Satish, Katla Ramesh, Nageswar Yadavalli Venkata Durga
Aqueous phase synthesis of polysubstituted pyrimidines/pyrrolidines catalyzed by β-cyclodextrin
European Journal of Chemistry  5(3), 541, 2014
DOI: 10.5155/eurjchem.5.3.541-544.1049
/


[7]. Manoj B. Gawande, Vasco D. B. Bonifácio, Rafael Luque, Paula S. Branco, Rajender S. Varma
Solvent-Free and Catalysts-Free Chemistry: A Benign Pathway to Sustainability
ChemSusChem  7(1), 24, 2014
DOI: 10.1002/cssc.201300485
/


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


How to cite


Katla, R.; Sabbavarapu, N.; Konkala, K.; Durga, N. Eur. J. Chem. 2012, 3(1), 119-124. doi:https://doi.org/10.5155/eurjchem.3.1.119-124.449
Katla, R.; Sabbavarapu, N.; Konkala, K.; Durga, N. Eur. J. Chem. A simple, solvent and catalyst-free green synthetic protocol for α-amino phosphonates. 2012, 3(1), 119-124. doi:https://doi.org/10.5155/eurjchem.3.1.119-124.449
Katla, R., Sabbavarapu, N., Konkala, K., & Durga, N. (2012). A simple, solvent and catalyst-free green synthetic protocol for α-amino phosphonates. European Journal of Chemistry, 3(1), 119-124. doi:https://doi.org/10.5155/eurjchem.3.1.119-124.449
Katla, Ramesh, Narayana Murthy Sabbavarapu, Karnakar Konkala, & Nageswar Yadavalli Venkata Durga. "A simple, solvent and catalyst-free green synthetic protocol for α-amino phosphonates." European Journal of Chemistry [Online], 3.1 (2012): 119-124. Web. 21 Apr. 2018
Katla, Ramesh, Sabbavarapu, Narayana, Konkala, Karnakar, AND Durga, Nageswar. "A simple, solvent and catalyst-free green synthetic protocol for α-amino phosphonates" European Journal of Chemistry [Online], Volume 3 Number 1 (31 March 2012)

DOI: https://doi.org/10.5155/eurjchem.3.1.119-124.449

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2018  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2018 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registred in USA.