European Journal of Chemistry

Utility of 2-cyano-N-(2-hydroxyethyl) acetamide in heterocyclic synthesis

Article Sidebar

PDF
Published: Jun 30, 2015
DOI: https://doi.org/10.5155/eurjchem.6.2.219-224.1223
Keywords:
Reactivity, Synthesis, Ethanolamine, Cyanoacetylation, Fused heterocycles, 2-Cyano-N-(2-hydroxyethyl) acetamide
Section
Review Article
Issue
Vol. 6 No. 2 (2015): June 2015
Dates
Received 2014-11-19
Accepted 2015-01-03
Published 2015-06-30


Main Article Content

Moustafa Ahmed Gouda
Chemistry Department, Faculty of Science, Mansoura University, Mansoura, 35516, Egypt
Meshal Abdulrahim Sabah
Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
Waled Khaled Aljuhani
Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
Ahmed Saleh El-Gahani
Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
Snad Abd El-Karem El-Enazi
Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
Salem Atalleh Al Enizi
Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
Majed Musallam Al-Balawi
Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia

Abstract

This review presents a systematic and comprehensive survey of the method of preparation and the chemical reactivity of 2-cyano-N-(2-hydroxyethyl) acetamide. The target compounds are important intermediates for the synthesis of a variety of synthetically useful and novel heterocyclic systems.


icon graph This Abstract was viewed 3011 times | icon graph Article PDF downloaded 1424 times

How to Cite
(1)
Gouda, M. A.; Sabah, M. A.; Aljuhani, W. K.; El-Gahani, A. S.; El-Enazi, S. A. E.-K.; Al Enizi, S. A.; Al-Balawi, M. M. Utility of 2-Cyano-N-(2-Hydroxyethyl) Acetamide in Heterocyclic Synthesis. Eur. J. Chem. 2015, 6, 219-224.

Article Details

Share
Links for Article


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

[1]. Elgemeie, G. H.; Elghandour, A. H.; Elzanate, A. M.; Ahmed, S. A. J. Chem. Soc. Perkin Trans I 1997, 21, 3285-3290

[2]. Milad, R. M.; Zaki, H. S.; Ibrahim, S. A. J. Chem. Res. (S) 1992, 5, 154-155.

[3]. Kim, C. K.; Zielinski, P. A.; Maggiulli, A. C. J. Org. Chem. 1984, 49, 5247-5250.
http://dx.doi.org/10.1021/jo00200a047

[4]. Elgemeie, G. H.; Elzanaty, A. M.; Elghandour, A. H.; Ahmed, S. A. Synth. Commun. 2006, 36, 825-834.
http://dx.doi.org/10.1080/00397910500449534

[5]. Dankova, E. F.; Bakulev, V. A.; Grishakov, A. N.; Mokrushin, V. S. Izv. Akad. Nauk. SSSR. Ser. Khim. 1988, 5, 1126-1128

[6]. Hawes, E. M.; Gorecki, D. K. J.; Gedir, G. G. J. Med. Chem, 1977, 20, 838-841.
http://dx.doi.org/10.1021/jm00216a021

[7]. Mijin, D.; Marinkovic, A. Synth. Commun. 2006, 36, 193-198.
http://dx.doi.org/10.1080/00397910500334421

[8]. Zhuravel, I.; Kovalenko, M. S.; Ivachtchenko, V. A.; Balakin, K. V.; Kazmirchuk, V. V. Bioorg. Med. Chem. 2005, 15, 5483-5487.
http://dx.doi.org/10.1016/j.bmcl.2005.08.081

[9]. Geissler, A. E.; Huppatz, J. L.; Phillips, J. N. Pesticide Sci. 1980, 11, 432-438.
http://dx.doi.org/10.1002/ps.2780110410

[10]. Roifman, C. M.; Aviv, G.; Alexander, L. PCT. Int. Appl. WO Patent, 2000, 0055, 128; Chem. Abstr. 2000, 133, 237695h.

[11]. Fahmy, H. T. Y.; Rostom, S. A. F.; Bekhit, A. A. Archiv der Pharm. 2002, 335, 213-322.
http://dx.doi.org/10.1002/1521-4184(200205)335:5<213::AID-ARDP213>3.0.CO;2-H

[12]. Ismail, M. M. F.; Ammar, Y. A.; El-Zahaby, H. S. A.; Eisa, S. I.; Barakat, S. E. Arch. Pharm. Life Sci. 2007, 340, 476-482.
http://dx.doi.org/10.1002/ardp.200600197

[13]. Doemling, A.; Wang, K.; Herdtweck, E. ACS Comb. Sci. 2012, 14, 316-322.
http://dx.doi.org/10.1021/co3000133

[14]. Horecker, B. L.; Kornberg, A. J. Biol. Chem. 1948, 175, 385-390.

[15]. Pearson, J. C.; Weaver, M. A.; Fleischer, J. C.; King, G. A. US 2006/115516.

[16]. Gillen, K. J.; Jamieson, C.; Maclean, J. K. F.; Moir, E. M.; Rankovic, Z. Patent; N. V. Organon, 2008, WO2008/3452.

[17]. Osdene, T. S.; Santilli, A. A.; McCardle, L. E.; Rosenthale, M. E. J. Med. Chem. 1967, 10, 165-171.
http://dx.doi.org/10.1021/jm00314a008

[18]. Tilak, B. D.; Ayyangar, N. R.; Rao, U. S. Indian J. Chem. B 1984, 23, 18-23.

[19]. Manidhar, D. M.; Rao, K. U. M.; Reddy, N. B.; Sundar, C. S.; Reddy, C. S. J. Korean. Chem. Soc. 2012, 56, 459-463.

[20]. Ivanov, E. I.; Kalayanov, G. D.; Yaroshchenko, I. M. Zh. Org. Khim. 1989, 25, 1975-1975.

[21]. Rideau, E.; Smith, T. K.; Stewart, G.; Westwood, N. J.; Zhou, L.; Rideau, E.; Smith, T. K. A. J. Med. Chem. 2013, 56, 796-806.
http://dx.doi.org/10.1021/jm301215e

[22]. Doemling, A.; Wang, K.; Herdtweck, E. ACS Comb. Sci. 2011, 13, 140-146.
http://dx.doi.org/10.1021/co100040z

[23]. Doemling, A.; Kim, D.; Wang, K. J. Comb. Chem. 2010, 12, 111-118
http://dx.doi.org/10.1021/cc9001586

[24]. Dannhardt, G.; Dominiak, P.; Laufer, S. Arch. Pharm. 1991, 324, 141-148.
http://dx.doi.org/10.1002/ardp.19913240303

[25]. Endo, S.; Hu, D.; Suyama, M.; Matsunaga, T.; Sugimoto, K.; Matsuya, Y.; El-Kabbani, O.; Kuwata, K.; Hara, A.; Kitade, Y.; Toyooka, N. Bioorg. Med. Chem. 2013, 21, 6378-6384.
http://dx.doi.org/10.1016/j.bmc.2013.08.059

[26]. Areias, F.; Costa, M.; Castro, M.; Brea, J.; Gregori-Puigjane, E.; Proenca, M. F.; Mestres, J.; Loza, M. I. Eur. J. Med. Chem. 2012, 54, 303-310.
http://dx.doi.org/10.1016/j.ejmech.2012.05.009

[27]. Santilli, A. A. Patent; American Home Products Corporation, 1981, US4266050.

[28]. Santilli, A. A.; Osdene, T. S. J. Org. Chem. 1964, 29, 2066-2068
http://dx.doi.org/10.1021/jo01030a539

[29]. Wang, K.; Kim, D.; Domling, A. J. Comb. Chem. 2010, 12, 111-118.
http://dx.doi.org/10.1021/cc9001586

[30]. Bol'but, A. V.; Kemskii, S. V.; Vovk, M. V. Russ. J. Org. Chem. 2014, 50, 685-690
http://dx.doi.org/10.1134/S107042801405011X

[31]. Santilli, A.; McCardle, L. E.; Rosenthale, M. E.; Osdene, T. S. J. Med. Chem. 1967, 10, 165-171.
http://dx.doi.org/10.1021/jm00314a008

[32]. Winkler, B.; Hueglin, D.; Eichin, K.; Ehrsam, L.; Marat, X.; Richard, H.; Kienzle, I. M.; Schroede, U. PCT Int. Appl., WO, 2013, 2013011480 A1 20130124, 10, 165.

[33]. Taunton, T.J. W.; Maglathlin, Jr. R.; Serafimova, I.; Cohen, M. S.; Miller, R.; Paavilainen, V.; McFarland, J.; Krishnan, S. US, US20130035325 A1.

[34]. Tuuttila, T.; Lipsonen, J.; Huuskonen, J.; Rissanen, K. Dyes Pigments 2008, 77, 357-362.
http://dx.doi.org/10.1016/j.dyepig.2007.06.003

Supporting Agencies

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 © 2025 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).